Compound for organic electric element, organic electric element using same, and electronic device comprising same organic electronic element

ABSTRACT

Provided are an organic electric element and an electronic device comprising the same. According to the present invention, the organic electric element uses a mixture of compounds as a phosphorescent host material which can achieve a high light-emitting efficiency and a low driving voltage and can greatly improve a lifespan in an organic electric element.

BACKGROUND Technical Field

The present invention relates to compound for organic electric element, organic electric element using the same, and an electronic device thereof.

Background Art

In general, organic light emitting phenomenon refers to a phenomenon that converts electronic energy into light energy by using an organic material. An organic electronic element using an organic light emitting phenomenon usually has a structure including an anode, a cathode, and an organic material layer interposed therebetween. Here, in order to increase the efficiency and stability of the organic electronic element, the organic material layer is often composed of a multi-layered structure composed of different materials, and for example, may include a hole injection layer, a hole transport layer, an emitting layer, an electron transport layer, an electron injection layer and the like.

A material used as an organic material layer in an organic electronic element may be classified into a light emitting material and a charge transport material, such as a hole injection material, a hole transport material, an electron transport material, an electron injection material and the like depending on its function.

In the case of a polycyclic compound containing a heteroatom, the difference in properties according to the material structure is so large that it is applied to various layers as a material of an organic electronic element. In particular, it has characteristics of different band gaps (HOMO, LUMO), electronical characteristics, chemical properties, and physical properties depending on the number of rings, fused positions and the type and arrangement of heteroatoms, therefore application development for layers of various organic electronic elements using the same has been progressed.

As a representative example thereof, in the following Patent Documents 1 to 4, the performance of the 5-membered cyclic compound in the polycyclic compound has been reported depending on the hetero type, arrangement, substituent type, fused position, and the like.

[Patent Document 1]: U.S. Pat. No. 5,843,607

[Patent Document 2]: Japanese Laid-Open Patent Publication No. 1999-162650 [Patent Document 3]: Korean Published Patent Application No. 2008-0085000 [Patent Document 4]: US Patent Publication No. 2010-0187977 [Patent Document 5]: Korean Published Patent Application No. 2011-0018340 [Patent Document 6]: Korean Published Patent Application No. 2009-0057711

Patent Documents 1 and 2 disclose an embodiment in which the indolecarbazole core in which the hetero atom in the 5-membered cyclic compound is composed only of nitrogen (N) is used, and an aryl group substituted or unsubstituted in N of indolocarbazole is used. However, in the prior invention 1, there exists only a simple aryl group substituted or unsubstituted with an alkyl group, an amino group, an alkoxy group, or the like as a substituent, so that the effect of the substituents of the polycyclic compounds was very poor to prove, and only the use as a hole transport material is described, and the use thereof as a phosphorescent host material is not described.

Patent Documents 3 and 4 disclose a compound in which pyridine, pyrimidine, triazine or the like containing an aryl group and N is substituted for an indolecarbazole core having a hetero atom N in the same 5-membered cyclic compound as in the above Patent Documents 1 and 2, however only the use examples for phosphorescent green host materials are described, and the performance for other heterocyclic compounds substituted for indolecarbazole core is not described.

In Patent Documents 5, Nitrogen (N), oxygen (O), sulfur (S), carbon and the like are described as heteroatom in the 5-membered cyclic compound, however there are only examples using the same heteroatom in the performance measurement data, the performance characteristics of a 5-membered cyclic compound containing a different heteroatom could not be confirmed.

Therefore, the patent document does not disclose solutions to low charge carrier mobility and low oxidation stability of a 5-membered cyclic compound containing same heteroatom.

When the 5-membered cyclic compound molecules are generally laminated, as the adjacent π-electrons increase, they have a strong electronical interaction, and this is closely related to the charge carrier mobility, particularly, the same 5-membered cyclic compound of N—N type has an edge-to-face morphology as an order of arrangement of molecules when molecules are laminated, otherwise a different 5-membered cyclic compound with different heteroatoms has an antiparallel cofacial π-stacking structure in which the packing structure of the molecules is opposite to each other, so that the arrangement order of the molecules becomes face-to-face morphology. It is reported that the steric effect of the substituent substituted on the asymmetrically arranged hetero atom N as the cause of this laminated structure causes relatively high carrier mobility and high oxidation stability (Org. Lett. 2008, 10, 1199).

In Patent Document 6, an example of using as a fluorescent host material for various polycyclic compounds having seven or more membered cyclic compounds has been reported.

As described above, the fused positions, the number of rings, the arrangement of heteroatoms, and characteristic change by type of the polycyclic compounds have not yet been sufficiently developed.

Particularly, in a phosphorescent organic electronic element using a phosphorescent dopant material, the LUMO and HOMO levels of the host material have a great influence on the efficiency and life span of the organic electronic element, this is because the charge balance control in the emitting layer, the quenching of the dopant, and the reduction in efficiency and life span due to light emission at the interface of the hole transport layer can be prevented, depending on whether electron and hole injection in the emitting layer can be efficiently controlled.

For fluorescent and phosphorescent host materials, recently we have been studying the increase of efficiency and life span of organic electronic elements using TADF (thermal activated delayed fluorescent), exciplex, etc., particularly, and many studies have been carried out to identify the energy transfer method from the host material to the dopant material.

Although there are various methods for identifying the energy transfer in the emitting layer for TADF (thermally activated delayed fluorescent) and exciplex, it can be easily confirmed by the PL lifetime (TRTP) measurement method.

The TRTP (Time Resolved Transient PL) measurement method is a method of observing a decay time over time after irradiating the host thin film with a pulsed light source, and therefore it is possible to identify the energy transfer method by observing the energy transfer and the lag time. The TRTP measurement can distinguish between fluorescence and phosphorescence, an energy transfer method in a mixed host material, an exciplex energy transfer method, and a TADF energy transfer method.

There are various factors affecting the efficiency and life span depending on the manner in which the energy is transferred from the host material to the dopant material, and the energy transfer method differs depending on the material, so that the development of stable and efficient host material for organic electronic element has not yet been sufficiently developed. Therefore, development of new materials is continuously required, and especially development of a host material for an emitting layer is urgently required.

DETAILED DESCRIPTION OF THE INVENTION Summary

The present invention has been proposed in order to solve the problems of the phosphorescent host material, and an object of the present invention is, by controlling the HOMO level of a host material of a phosphorescent emitting organic electronic element including a phosphorescent dopant, to provide a compound capable of controlling charge balance and of improving efficiency and life span in an emitting layer, and an organic electronic element using the same and an electronic device thereof.

Technical Solution

In order to control the efficient hole injection and electron injection in the emitting layer of the phosphorescence emitting organic electronic element, by containing a specific second host material in combination to a specific first host material, it is possible to reduce the energy barrier of the emitting layer and the adjacent layer, the charge balance in the emitting layer is maximized, thereby providing high efficiency and high life of the organic electronic device.

The present invention provides an organic electronic element comprising a first electrode, a second electrode, and an organic material layer formed between the first electrode and the second electrode, wherein the organic material layer includes an emitting layer, and the emitting layer includes a first host compound represented by the following Formula (1) and a second host compound represented by the following Formula (2).

The present invention also provides an organic electric element using the compound represented by the above formulas and an electronic device thereof.

Effects of the Invention

By using the mixture according to the present invention as a phosphorescent host material, it is possible to achieve a high luminous efficiency and a low driving voltage of an organic electric element, and the life span of the device can be greatly improved.

BRIEF DESCRIPTION OF THE DRAWINGS

FIG. 1 is an illustration of an organic electroluminescent device according to the present invention.

100: organic electric element, 110: substrate 120: the first electrode (anode), 130: the hole injection layer 140: the hole transport layer, 141: a buffer layer 150: the emitting layer, 151: the emitting auxiliary layer 160: the electron transport layer, 170: the electron injection layer 180: the second electrode (cathode)

FIG. 2 shows 1 H NMR result of compound 3-6.

FIG. 3 shows 13 C NMR result of compound 3-6.

FIG. 4 shows 1 H NMR result of compound 3-8.

FIG. 5 shows 13 C NMR result of compound 3-8.

FIG. 6 shows 1 H NMR result of compound 3-7.

FIG. 7 shows 13 C NMR result of compound 3-7.

FIG. 8 shows 1 H NMR result of compound 3-101 (compound P1-1).

FIG. 9 shows 13 C NMR result of compound 3-101 (compound P1-1).

DETAILED DESCRIPTION

Hereinafter, some embodiments of the present invention will be described in detail.

Further, in the following description of the present invention, a detailed description of known functions and configurations incorporated herein will be omitted when it may make the subject matter of the present invention rather unclear.

In addition, terms, such as first, second, A, B, (a), (b) or the like may be used herein when describing components of the present invention. Each of these terminologies is not used to define an essence, order or sequence of a corresponding component but used merely to distinguish the corresponding component from other component(s). It should be noted that if a component is described as being “connected”, “coupled”, or “connected” to another component, the component may be directly connected or connected to the other component, but another component may be “connected”, “coupled” or “connected” between each component.

As used in the specification and the accompanying claims, unless otherwise stated, the following is the meaning of the term as follows.

Unless otherwise stated, the term “halo” or “halogen”, as used herein, includes fluorine, bromine, chlorine, or iodine.

Unless otherwise stated, the term “alkyl” or “alkyl group”, as used herein, has a single bond of 1 to 60 carbon atoms, and means saturated aliphatic functional radicals including a linear alkyl group, a branched chain alkyl group, a cycloalkyl group (alicyclic), an cycloalkyl group substituted with a alkyl or an alkyl group substituted with a cycloalkyl.

Unless otherwise stated, the term “haloalkyl” or “halogen alkyl”, as used herein, includes an alkyl group substituted with a halogen.

Unless otherwise stated, the term “heteroalkyl”, as used herein, means alkyl substituted one or more of carbon atoms consisting of an alkyl with hetero atom.

Unless otherwise stated, the term “alkenyl” or “alkynyl”, as used herein, has double or triple bonds of 2 to 60 carbon atoms, but is not limited thereto, and includes a linear or a branched chain group.

Unless otherwise stated, the term “cycloalkyl”, as used herein, means alkyl forming a ring having 3 to 60 carbon atoms, but is not limited thereto.

Unless otherwise stated, the term “alkoxyl group”, “alkoxy group” or “alkyloxy group”, as used herein, means an oxygen radical attached to an alkyl group, but is not limited thereto, and has 1 to 60 carbon atoms.

Unless otherwise stated, the term “alkenoxyl group”, “alkenoxy group”, “alkenyloxyl group” or “alkenyloxy group”, as used herein, means an oxygen radical attached to an alkenyl group, but is not limited thereto, and has 2 to 60 carbon atoms.

Unless otherwise stated, the term “aryloxyl group” or “aryloxy group”, as used herein, means an oxygen radical attached to an aryl group, but is not limited thereto, and has 6 to 60 carbon atoms.

Unless otherwise stated, the term “aryl group” or “arylene group”, as used herein, has 6 to 60 carbon atoms, but is not limited thereto. Herein, the aryl group or arylene group means a monocyclic and polycyclic aromatic group, and may also be formed in conjunction with an adjacent group. Examples of “aryl group” may include a phenyl group, a biphenyl group, a fluorene group, or a spirofluorene group.

The prefix “aryl” or “ar” means a radical substituted with an aryl group. For example, an arylalkyl may be an alkyl substituted with an aryl, and an arylalenyl may be an alkenyl substituted with aryl, and a radical substituted with an aryl has a number of carbon atoms as defined herein.

Also, when prefixes are named subsequently, it means that substituents are listed in the order described first. For example, an arylalkoxy means an alkoxy substituted with an aryl, an alkoxylcarbonyl means a carbonyl substituted with an alkoxyl, and an arylcarbonylalkenyl also means an alkenyl substituted with an arylcarbonyl, wherein the arylcarbonyl may be a carbonyl substituted with an aryl.

Unless otherwise stated, the term “heteroalkyl”, as used herein, means alkyl containing one or more of hetero atoms. Unless otherwise stated, the term “heteroaryl group” or “heteroarylene group”, as used herein, means a C2 to C60 aryl containing one or more of hetero atoms or arylene group, but is not limited thereto, and includes at least one of monocyclic and polycyclic rings, and may also be formed in conjunction with an adjacent group.

Unless otherwise stated, the term “heterocyclic group”, as used herein, contains one or more heteroatoms, but is not limited thereto, has 2 to 60 carbon atoms, includes any one of monocyclic and polycyclic rings, and may include heteroaliphadic ring and/or heteroaromatic ring. Also, the heterocyclic group may also be formed in conjunction with an adjacent group. Unless otherwise stated, the term “heteroatom”, as used herein, represents at least one of N, O, S, P, or Si.

Also, the term “heterocyclic group” may include a ring containing SO₂ instead of carbon consisting of cycle. For example, “heterocyclic group” includes compound below.

Unless otherwise stated, the term “aliphatic”, as used herein, means an aliphatic hydrocarbon having 1 to 60 carbon atoms, and the term “aliphatic ring”, as used herein, means an aliphatic hydrocarbon ring having 3 to 60 carbon atoms.

Unless otherwise stated, the term “ring”, as used herein, means an aliphatic ring having 3 to 60 carbon atoms, or an aromatic ring having 6 to 60 carbon atoms, or a hetero ring having 2 to 60 carbon atoms, or a fused ring formed by the combination of them, and includes a saturated or unsaturated ring.

Other hetero compounds or hetero radicals other than the above-mentioned hetero compounds include, but are not limited thereto, one or more heteroatoms.

Unless otherwise stated, the term “carbonyl”, as used herein, is represented by —COR′, wherein R′ may be hydrogen, an alkyl having 1 to 20 carbon atoms, an aryl having 6 to 30 carbon atoms, a cycloalkyl having 3 to 30 carbon atoms, an alkenyl having 2 to 20 carbon atoms, an alkynyl having 2 to 20 carbon atoms, or the combination of these.

Unless otherwise stated, the term “ether”, as used herein, is represented by —R—O—R′, wherein R or R′ may be independently hydrogen, an alkyl having 1 to 20 carbon atoms, an aryl having 6 to 30 carbon atoms, a cycloalkyl having 3 to 30 carbon atoms, an alkenyl having 2 to 20 carbon atoms, an alkynyl having 2 to 20 carbon atoms, or the combination of these.

Unless otherwise stated, the term “substituted or unsubstituted”, as used herein, means that substitution is substituted by at least one substituent selected from the group consisting of, but is not limited thereto, deuterium, halogen, an amino group, a nitrile group, a nitro group, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxyl group, a C₁-C₂₀ alkylamine group, a C₁-C₂₀ alkylthiopen group, a C₆-C₂₀ arylthiopen group, a C₂-C₂₀ alkenyl group, a C₂-C₂₀ alkynyl group, a C₃-C₂₀ cycloalkyl group, a C₆-C₂₀ aryl group, a C₆-C₂₀ aryl group substituted by deuterium, a C₈-C₂₀ arylalkenyl group, a silane group, a boron group, a germanium group, and a C₂-C₂₀ heterocyclic group.

Unless otherwise expressly stated, the Formula used in the present invention, as used herein, is applied in the same manner as the substituent definition according to the definition of the exponent of the following Formula.

Wherein, when a is an integer of zero, the substituent R¹ is absent, that is, when a is 0, it means that hydrogen is bonded to all the carbons forming the benzene ring. In this case, the sign of the hydrogen bonded to the carbon may be omitted and the formula or compound may be described.

When a is an integer of 1, the sole substituent R¹ is linked to any one of the carbon constituting the benzene ring, and when a is an integer of 2 or 3, they are respectively combined as follows, and when a is an integer from 4 to 6, it is bonded to the carbon of the benzene ring in a similar manner, and when a is an integer of 2 or more, R¹ may be the same or different from each other.

Unless otherwise expressly stated, the terms “ortho”, “meta”, and “para” used in the present invention refer to the substitution positions of all substituents, and the ortho position indicates the position of the substituent immediately adjacent to the compound, for example, when benzene is used, it means 1 or 2 position, and the meta position is the next substitution position of the neighbor substitution position, when benzene as an example stands for 1 or 3 position, and the para position is the next substitution position of the meta position, which means 1 and 4 position when benzene is taken as an example. A more detailed example of the substitution position is as follows, and it can be confirmed that the ortho-, and meta-position are substituted by non-linear type and para-positions are substituted by linear type.

Example of Ortho-Position

Example of Meta-Position

Example of Para-Position

Hereinafter, a compound according to an aspect of the present invention and an organic electric element comprising the same will be described.

The present invention provides an organic electric element comprising a first electrode, a second electrode, and an organic material layer formed between the first electrode and the second electrode, wherein the organic material layer comprises an emitting layer, wherein the emitting layer is a phosphorescent light emitting layer and comprises a first host compound represented by Formula (1) and a second host compound represented by Formula (2).

{In Formulas (1) and (2),

1) Ar¹, Ar², Ar³, and Ar⁴ are each independently selected from the group consisting of a C₆-C₆₀ aryl group; a fluorenyl group; a C₂-C₆₀ heterocyclic group including at least one hetero atom of O, N, S, Si or P; a fused ring group of a C₃-C₆₀ aliphatic ring and a C₆-C₆₀ aromatic ring; a C₁-C₅₀ alkyl group; a C₂-C₂₀ alkenyl group; a C₂-C₂₀ alkynyl group; a C₁-C₃₀ alkoxyl group; a C₆-C₃₀ aryloxy group;

2) c and e are integer of 0 to 10, and d is an integer of 0 to 2, and R³, R⁴ and R⁵ are the same or different from each other, and are each independently selected from the group consisting of deuterium; halogen; a C₆-C₆₀ aryl group; a fluorenyl group; a C₂-C₆₀ heterocyclic group including at least one heteroatom of O, N, S, Si or P; a fused ring group of a C₃-C₆₀ aliphatic ring and a C₆-C₆₀ aromatic ring; a C₁-C₅₀ alkyl group; a C₂-C₂₀ alkenyl group; a C₂-C₂₀ alkynyl group; a C₁-C₃₀ alkoxyl group; a C₆-C₃₀ aryloxy group; and -L′-N(R_(a))(R_(b)); (wherein, L′ is selected from the group consisting of a single bond; a C₆-C₆₀ arylene group; a fluorenylene group; a fused ring group of a C₃-C₆₀ aliphatic ring and a C₆-C₆₀ aromatic ring; and a C₂-C₆₀ heterocyclic, and R_(a) and R_(b) are independently selected from the group consisting of a C₆-C₆₀ aryl group; a fluorenyl group; a fused ring group of a C₃-C₆₀ aliphatic ring and a C₆-C₆₀ aromatic ring; and a C₂-C₆₀ heterocyclic group containing at least one hetero atom of O, N, S, Si, or P), or in case c, d and e are 2 or more, R³, R⁴ and R⁵ are each in plural being the same or different, and a plurality of R³ or a plurality of R⁴ or a plurality of R⁵ combine to each other to form a ring.

When Ar¹, Ar², Ar³, and Ar⁴, and R¹, R², R³, R⁴ and R⁵ are aryl groups, it is preferably a C₆-C₃₀ aryl group, more preferably a C₆-C₁₈ aryl group,

When Ar¹, Ar², Ar³, and Ar⁴, and R¹, R², R³, R⁴ and R⁸ are heterocyclic groups, it is preferably a C₂-C₄₀ heterocyclic group, more preferably a C₂-C₃₀ heterocyclic group, still more preferably a C₂-C₂₀ heterocyclic group.

When Ar¹, Ar², Ar³, and Ar⁴, and R¹, R², R³, R⁴ and R⁸ are aryl groups, specific examples thereof include phenyl, biphenyl, terphenyl, stilbenyl, naphthyl, anthracenyl, phenanthryl, pyrenyl, perylenyl, a quaterphenyl group, a klycenyl group, and the like

When Ar¹, Ar², Ar³, and Ar⁴, and R¹, R², R³, R⁴ and R⁸ are heterocyclic groups, specific examples thereof include a thiophene group, a furan group, a pyrrolyl group, an imidazole group, a thiazole group, an oxazole group, an oxadiazole group, a triazole group, a pyridyl group, a bipyridyl group, a pyrimidyl group, a triazine group, a pyrazine group, a triazole group, an acridyl group, a pyridazine group, a pyrazinyl group, a quinolinyl group, a quinazolinyl group, a quinoxalinyl group, a benzoquinoxaline, dibenzoquinoxaline, a phthalazinyl group, a pyridopyrimidinyl group, a pyridopyrazinyl group, a pyrazinopyrazinyl group, an isoquinoline group, an indole group, a carbazole group, indolocarbazole, acridine, phenoxazine, benzopyridazine, benzopyrimidine, carboline, benzocarboline, benzoxazole group, a benzoimidazole group, a benzothiazole group, a benzocarbazole group, a benzothiophene group, a Dibenzothiophene group, a benzofuranyl group, a phenanthroline group, a thiazolyl group, an isoxazolyl group, an oxadiazolyl group, a thiadiazolyl group, a benzothiazolyl group, a phenothiazinyl group and a dibenzofuranyl group, thienothiophene, benzothienopyridine, benzothienopyrimidine, Benzofuropyrimidine, dimethylbenzoindenopyrimidine, phenanthropuropyrimidine, Naphthopuroppyrimidine, naphthothienopyrimidine, dibenzothiophene, thianthrene, Dihydrobenzothiophenopyrazine, dihydrobenzofuropyrazine, and the like, but are not limited thereto.

3) L¹, L², L³ and L⁴ are selected from the group consisting of a single bond, a C₆-C₆₀ arylene group, and a fluorenylene group; a fused ring group of a C₃-C₆₀ aliphatic ring and a C₆-C₆₀ aromatic ring; and a C₂-C₆₀ heterocyclic group;

4) A and B are each independently a C₆-C₆₀ aryl group or a C₂-C₂₀ heterocyclic group, wherein both A and B are a substituted or unsubstituted C₆ aryl group (phenyl group), d is 2, and R⁴s are bonded to each other to form a ring to form an aromatic or hetero ring,

5) i and j are 0 or 1, with the proviso that i+j is 1 or more, and when i or j is 0, it means a direct bond,

6) X¹ and X² are independently NR′, O, S, or CR′R″;

wherein R′ and R″ are independently hydrogen; a C₆-C₆₀ aryl group; a fluorenyl group; a C₃-C₆₀ heterocyclic group; or a C₁-C₅₀ alkyl group; wherein R′ and R″ may combine to each other to form a spiro,

(wherein, the aryl group, fluorenyl group, arylene group, heterocyclic group, fused ring group, alkyl group, alkenyl group, alkoxy group and aryloxy group may be substituted with one or more substituents selected from the group consisting of deuterium; halogen; a silane group substituted or unsubstituted with C₁-C₂₀ alkyl group or C₆-C₂₀ aryl group; siloxane group; boron group; germanium group; cyano group; nitro group; -L′-N(R_(a))(R_(b)); a C₁-C₂₀ alkylthio group; C₁-C₂₀ alkoxyl group; C₁-C₂₀ alkyl group; C₂-C₂₀ alkenyl group; C₂-C₂₀ alkynyl group; C₆-C₂₀ aryl group; C₆-C₂₀ aryl group substituted with deuterium; a fluorenyl group; C₂-C₂₀ heterocyclic group; C₃-C₂₀ cycloalkyl group; C₇-C₂₀ arylalkyl group and C₈-C₂₀ arylalkenyl group, wherein the substituents may combine each other and form a saturated or unsaturated ring, wherein the term ‘ring’ means C₃-C₆₀ aliphatic ring or C₆-C₆₀ aromatic ring or a C₂-C₆₀ heterocyclic ring or a fused ring formed by the combination of thereof.)}

In addition, the present invention provides the compounds represented by Formulas (1) and (2).

The first host compound represented by Formula (1) is represented by any one of the following Formulas (3) to (5).

{In Formulas (3) to (5),

1) L¹, L³, L⁴, L′, R^(a), R^(b), Ar² and Ar³ are the same as defined above,

2) X³ is O or S,

3) a is an of 0 to 4, and b is an integer of 0 to 3, and R¹ and R² are the same or different from each other, and are each independently selected from the group consisting of deuterium; halogen; a C₆-C₆₀ aryl group; a fluorenyl group; a C₂-C₆₀ heterocyclic group including at least one heteroatom of O, N, S, Si or P; a fused ring group of a C₃-C₆₀ aliphatic ring and a C₆-C₆₀ aromatic ring; a C₁-C₅₀ alkyl group; a C₂-C₂₀ alkenyl group; a C₂-C₂₀ alkynyl group; a C₁-C₃₀ alkoxyl group; a C₆-C₃₀ aryloxy group; and -L′-N(R_(a))(R_(b)); or in case a and b are 2 or more, and R¹ and R² are each in plural being the same or different, and a plurality of R¹ or a plurality of R² combine to each other to form a ring.}

The compound represented by Formula (1) is represented by any one of the following Formulas (6) to (14).

{In Formulas (6) to (14)

L¹, L³, L⁴, Ar², Ar³, R¹, R², a and b are the same as defined in Formula (1)}

The first host compound represented by Formula (1) is represented by any one of the following Formulas (15) to (23).

{In Formulas (15) to (23),

L¹, L³, L⁴, Ar², Ar³, R¹, R², a and b are the same as defined in Formula (1)}

The first host compound represented by Formula (1) is represented by any one of the following Formulas (24) to (26).

{In Formulas (24) to (26),

1) L¹, L³, L⁴, L′, R^(a), R^(b), Ar² and Ar³ are the same as defined above,

2) Ar⁵ and Ar⁶ are each independently selected from the group consisting of a C₆-C₆₀ aryl group; a C₂-C₆₀ heterocyclic group including at least one heteroatom of O, N, S, Si or P; a fused ring group of a C₃-C₆₀ aliphatic ring and a C₆-C₆₀ aromatic ring; a C₁-C₅₀ alkyl group; a C₂-C₂₀ alkenyl group; a C₂-C₂₀ alkynyl group; a C₁-C₃₀ alkoxyl group; a C₆-C₃₀ aryloxy group; and -L′-N(R_(a))(R_(b))}

In Formula (1) of the present invention, L¹, L³ and L⁴ are any one of the following Formulas (A-1) to (A-12).

{In Formulas (A-1) to (A-12),

1) a′, c′, d′ and e′ are an integer of 0 to 4; and b′ is an integer of 0 to 6; and f and g′ are integer of 0 to 3; and h′ is an integer of 0 to 1,

2) R⁶, R⁷ and R⁸ are the same or different from each other, and are each independently selected from the group consisting of deuterium; halogen; a C₆-C₆₀ aryl group; a fluorenyl group; a C₂-C₆₀ heterocyclic group including at least one heteroatom of O, N, S, Si or P; a fused ring group of a C₃-C₆₀ aliphatic ring and a C₆-C₆₀ aromatic ring; a C₁-C₅₀ alkyl group; a C₂-C₂₀ alkenyl group; a C₂-C₂₀ alkynyl group; a C₁-C₃₀ alkoxyl group; a C₆-C₃₀ aryloxy group; and -L′-N(R_(a))(R_(b)); or wherein f′ and g′ are two or more, R⁶, R⁷ and R⁸ are the same as or different from each other, and a plurality of R⁶ or a plurality of R⁷ or adjacent R⁶ and R⁷ may combine to each other to form an aromatic or a heteroaromatic ring,

3) Y is NR′, O, S or CR′R″,

L′, R_(a), R_(b), R¹ and R⁷ are the same as defined above,

4) Z¹, Z² and Z³ are CR′ or N and at least one is N.}

In one embodiment of the present invention, at least one of L¹, L³, and L⁴ in Formula (1) is a phenyl group and is substituted with an m (meta)-position.

The present invention provides an organic electric element wherein the second host compound represented by Formula (2) comprises a compound represented by the following Formula (27) or (28).

{In Formulas (27) to (28),

wherein R³, R⁴, R⁵, Ar⁴, L², c, d, e, A, B, X¹ and X² are the same as defined in Formula (2).}

The present invention also provides an organic electric element comprising a compound wherein A and B in Formula (2) are selected from the group consisting of the following Formulas (B-1) to (B-7).

{In Formulas (B-1) to (B-7),

1) Z⁴ to Z⁵⁰ are CR′ or N,

2) R′ is the same as defined above,

3) * indicates the position to be condensed.}

As another example, the present invention provides a compound wherein the second host compound represented by Formula (2) includes a compound represented by any of the following Formulas (29) to (48).

{In Formulas (29) to (48),

Ar⁴, X¹, X², R³, R⁴, R⁵, L², c, d, and e are the same as defined above.}

In the present invention, the second host compound represented by Formula (2) comprises any of compounds represented by the following Formulas (49) to (56).

{In Formulas (49) to (56),

R³, R⁴, R⁵, R′, R″, L², Ar⁴, c, d, e, A and B are the same as defined above.}

As a specific example of the present invention, the first host compound represented by Formula (1) is one of the following Compounds 1-1′ to 1-82′.

Also, the second host compound represented by Formula (2) is one of the following Compounds 3-1 to 3-100, P1-1 to P1-45, P2-1 to P2-10, P3-1 to P3-45, P4-1 to P4-10. P5-1 to P5-45, P6-1 to P6-15.

Referring to FIG. 1, the organic electric element (100) according to the present invention includes a first electrode (120) formed on a substrate (110), a second electrode (180), and an organic material layer including the compound represented by Formula (1) between the first electrode (120) and the second electrode (180). Here, the first electrode (120) may be an anode (positive electrode), and the second electrode (180) may be a cathode (negative electrode). In the case of an inverted organic electric element, the first electrode may be a cathode, and the second electrode may be an anode.

The organic material layer may include a hole injection layer (130), a hole transport layer (140), an emitting layer (150), an electron transport layer (160), and an electron injection layer (170) formed in sequence on the first electrode (120). Here, the remaining layers except the emitting layer (150) may not be formed. The organic material layer may further include a hole blocking layer, an electron blocking layer, an emitting-auxiliary layer (151), an electron transport auxiliary layer, a buffer layer (141), etc., and the electron transport layer (160) and the like may serve as a hole blocking layer.

Although not shown, the organic electric element according to the present invention may further include a protective layer formed on at least one side of the first and second electrodes, which is a side opposite to the organic material layer.

Otherwise, even if the same core is used, the band gap, the electrical characteristics, the interface characteristics, and the like may vary depending on which substituent is bonded at which position, therefore the choice of core and the combination of sub-substituents associated therewith is also very important, and in particular, when the optimal combination of energy levels and Ti values and unique properties of materials (mobility, interfacial characteristics, etc.) of each organic material layer is achieved, a long life span and high efficiency can be achieved at the same time.

The organic electroluminescent device according to an embodiment of the present invention may be manufactured using a PVD (physical vapor deposition) method. For example, a metal or a metal oxide having conductivity or an alloy thereof is deposited on a substrate to form a cathode, and the organic material layer including the hole injection layer (130), the hole transport layer (140), the emitting layer (150), the electron transport layer (160), and the electron injection layer (170) is formed thereon, and then depositing a material usable as a cathode thereon can manufacture an organic electroluminescent device according to an embodiment of the present invention.

In addition, an emission auxiliary layer (151) may be further formed between the hole transport layer (140) and the emitting layer (150), and an electron transport auxiliary layer may be further formed between the emitting layer (150) and the electron transport layer (160).

The present invention may further include a light efficiency enhancing layer formed on at least one of the opposite side to the organic material layer among one side of the first electrode, or one of the opposite side to the organic material layer among one side of the second electrode.

Also, the present invention provides the organic electric element wherein the organic material layer is formed by one of a spin coating process, a nozzle printing process, an inkjet printing process, a slot coating process, a dip coating process or a roll-to-roll process, and since the organic material layer according to the present invention can be formed by various methods, the scope of the present invention is not limited by the method of forming the organic material layer.

As another specific example, the present invention provides an organic electric element wherein the emitting layer in the organic material layer is a phosphorescent light emitting layer.

The compounds represented by Formula (1) and (2) are mixed in a ratio of any one of 1:9 to 9:1 to be included in the emitting layer of the organic material layer.

The compound represented by Formula (1) and (2) are mixed in a ratio of any one of 1:9 to 5:5 to be included in the emitting layer of the organic material layer. More preferably, the mixing ratio of the compound represented by Formula (1) and (2) is 2:8 or 3:7 to be included in the emitting layer.

The organic electric element according to an embodiment of the present invention may be a front emission type, a back emission type, or a both-sided emission type, depending on the material used.

WOLED (White Organic Light Emitting Device) has advantages of high resolution realization and excellent fairness, and can be manufactured using conventional LCD color filter technology. Various structures for a white organic light emitting device mainly used as a backlight device have been proposed and patented. Representatively, there are side-by-side arrangement of the radiation part of the R (red), G (green) and B (blue), a stacking method in which R, G, and B emitting layers are laminated on top and bottom, electroluminescence by the blue (B) organic emitting layer and, by using the light from this, a color conversion material (CCM) method using a photo-luminescence of an inorganic phosphor, etc., and the present invention may be applied to such WOLED.

The present invention also provides an electronic device comprising a display device including the organic electric element; and a control unit for driving the display device.

According to another aspect, the present invention provides an display device wherein the organic electric element is at least one of an OLED, an organic solar cell, an organic photo conductor, an organic transistor (organic TFT) and an element for monochromic or white illumination. Here, the electronic device may be a wired/wireless communication terminal which is currently used or will be used in the future, and covers all kinds of electronic devices including a mobile communication terminal such as a cellular phone, a personal digital assistant (PDA), an electronic dictionary, a point-to-multipoint (PMP), a remote controller, a navigation unit, a game player, various kinds of TVs, and various kinds of computers.

Hereinafter, Synthesis Examples of the compound represented by Formula (1) of the present invention and preparation examples of the organic electric element of the present invention will be described in detail by way of example, but are not limited to the following examples.

Synthesis Example 1

The final products 1 represented by Formula (1) of the present invention can be synthesized by reaction between Sub 1 and Sub 2 as illustrated in the following Reaction Scheme 1.

Examples of Sub 1

Examples of Sub 1 of Reaction Scheme 1 are as follows, but are not limited thereto.

Synthesis Examples of Sub 2 Sub 1-20 Sub 1-21 Sub 1-22

Sub 2 of reaction scheme 1 can be synthesized by the reaction path of the following reaction scheme 2, but is not limited thereto.

Examples of Sub 2-1

In a round bottom flask, Aniline (15 g, 161.1 mmol), 1-bromonaphthalene (36.7 g, 177.2 mmol), Pd₂(dba)₃ (7.37 g, 8.05 mmol), P(t-Bu)₃ (3.26 g, 16.1 mmol), NaOt-Bu (51.08 g, 531.5 mmol), toluene (1690 mL) were added, and stirred at 100° C. After the reaction was completed, the reaction mixture was extracted with CH₂Cl₂ and water. The organic layer was dried over MgSO₄ and concentrated. The resulting compound was separated by silicagel column chromatography and recrystallized to obtain 25.4 g of Sub 2-1. (yield: 72%)

Examples of Sub 2-26

In a round bottom flask, [1,1′-biphenyl]-4-amine (15 g, 88.6 mmol), 2-(4-bromophenyl)-9,9-diphenyl-9H-fluorene (46.2 g, 97.5 mmol), Pd₂(dba)₃ (4.06 g, 4.43 mmol), P(t-Bu)₃ (1.8 g, 8.86 mmol), NaOt-Bu (28.1 g, 292.5 mmol), toluene (931 mL) were tested in the same manner as Sub 2-1 to obtain 34.9 g of Sub 2-26. (yield: 70%)

Examples of Sub 2-40

In a round bottom flask, naphthalen-1-amine (15 g, 104.8 mmol), 2-bromodibenzo[b,d]thiophene (30.3 g, 115.2 mmol), Pd₂(dba)₃ (4.8 g, 5.24 mmol), P(t-Bu)₃ (2.12 g, 10.48 mmol), NaOt-Bu (33.22 g, 345.7 mmol), toluene (1100 mL) were tested in the same manner as Sub 2-1 to obtain 24.9 g of Sub 2-40. (yield: 73%)

Examples of Sub 2-51

In a round bottom flask, 4-(dibenzo[b,d]furan-2-yl)aniline (15 g, 57.85 mmol), 2-bromodibenzo[b,d]furan (15.7 g, 63.63 mmol), Pd₂(dba)₃ (2.65 g, 2.89 mmol), P(t-Bu)₃ (1.17 g, 5.78 mmol), NaOt-Bu (18.35 g, 190.9 mmol), toluene (607 mL) were tested in the same manner as Sub 2-1 to obtain 17.2 g of Sub 2-51. (yield: 70%)

The following Sub 2-1 to Sub 2-52 were synthesized in the same manner as in the synthesis method, but Sub 2 is not limited thereto.

TABLE 1 compound FD-MS comound FD-MS Sub 2-1 m/z = 219.10 (C₁₆H₁₃N = 219.28) Sub 2-2 m/z = 295.14 (C₂₂H₁₇N = 295.38) Sub 2-3 m/z = 269.12 (C₂₀H₁₅N = 269.34) Sub 2-4 m/z = 169.09 (C₁₂H₁₁N = 169.22) Sub 2-5 m/z = 245.12 (C₁₈H₁₅N = 245.32) Sub 2-6 m/z = 321.15 (C₂₄H₁₉N = 321.41) Sub 2-7 m/z = 269.12 (C₂₀H₁₅N = 269.34) Sub 2-8 m/z = 345.15 (C₂₆H₁₉N = 345.44) Sub 2-9 m/z = 345.15 (C₂₆H₁₉N = 345.44) Sub 2-10 m/z = 325.18 (C₂₄H₂₃N = 325.45) Sub 2-11 m/z = 397.18 (C₃₀H₂₃N = 397.51) Sub 2-12 m/z = 447.20 (C₃₄H₂₅N = 447.57) Sub 2-13 m/z = 371.17 (C₂₈H₂₁N = 371.47) Sub 2-14 m/z = 421.18 (C₃₂H₂₃N = 421.53) Sub 2-15 m/z = 295.14 (C₂₂H₁₇N = 295.38) Sub 2-16 m/z = 397.18 (C₃₀H₂₃N = 397.51) Sub 2-17 m/z = 321.15 (C₂₄H₁₉N = 321.41) Sub 2-18 m/z = 245.12 (C₁₈H₁₅N = 245.32) Sub 2-19 m/z = 321.15 (C₂₄H₁₉N = 321.41) Sub 2-20 m/z = 321.15 (C₂₄H₁₉N = 321.41) Sub 2-21 m/z = 371.17 (C₂₈H₂₁N = 371.47) Sub 2-22 m/z = 421.18 (C₃₂H₂₃N = 421.53) Sub 2-23 m/z = 395.17 (C₃₀H₂₁N = 395.49) Sub 2-24 m/z = 473.21 (C₃₆H₂₇N = 473.61) Sub 2-25 m/z = 369.15 (C₂₈H₁₉N = 369.46) Sub 2-26 m/z = 561.25 (C₄₃H₃₁N = 561.71) Sub 2-27 m/z = 411.20 (C₃₁H₂₅N = 411.54) Sub 2-28 m/z = 459.20 (C₃₅H₂₅N = 459.58) Sub 2-29 m/z = 483.20 (C₃₇H₂₅N = 483.60) Sub 2-30 m/z = 375.16 (C₂₇H₂₁NO = 375.46) Sub 2-31 m/z = 475.19 (C₃₅H₂₅NO = 475.58) Sub 2-32 m/z = 575.22 (C₄₃H₂₉NO = 575.70) Sub 2-33 m/z = 533.21 (C₄₁H₂₇N = 533.66) Sub 2-34 m/z = 485.21 (C₃₇H₂₇N = 485.62) Sub 2-35 m/z = 361.18 (C₂₇H₂₃N = 361.48) Sub 2-36 m/z = 485.21 (C₃₇H₂₇N = 485.62) Sub 2-37 m/z = 499.19 (C₃₇H₂₅NO = 499.60) Sub 2-38 m/z = 439.19 (C₃₂H₂₅NO = 439.55) Sub 2-39 m/z = 335.13 (C₂₄H₁₇NO = 335.40) Sub 2-40 m/z = 325.09 (C₂₂H₁₅NS = 325.43) Sub 2-41 m/z = 427.14 (C₃₀H₂₁NS = 427.56) Sub 2-42 m/z = 461.18 (C₃₄H₂₃NO = 461.55) Sub 2-43 m/z = 349.11 (C₂₄H₁₅NO₂ = 349.38) Sub 2-44 m/z = 381.06 (C₂₄H₁₅NS₂ = 381.51) Sub 2-45 m/z = 457.10 (C₃₀H₁₉NS₂ = 457.61) Sub 2-46 m/z = 533.13 (C₃₆H₂₃NS₂ = 533.70) Sub 2-47 m/z = 353.10 (C₂₂H₁₅N₃S = 353.44) Sub 2-48 m/z = 327.0 (C₂₀H₁₃N₃S = 327.40) Sub 2-49 m/z = 375.11 (C₂₆H₁₇NS = 375.48) Sub 2-50 m/z = 411.16 (C₃₀H₂₁NO = 411.49) Sub 2-51 m/z = 425.14 (C₃₀H₁₉NO₂ = 425.48) Sub 2-52 m/z = 475.16 (C₃₄H₂₁NO₂ = 475.54)

Synthesis Examples of Final Product

Synthesis 1-1′

In a round bottom flask, di([1,1′-biphenyl]-4-yl)amine (10 g, 31.1 mmol), 4-bromo-1,1′-biphenyl (8 g, 34.2 mmol), Pd₂(dba)₃ (1.42 g, 1.56 mmol), P(t-Bu)₃ (0.63 g, 3.11 mmol), NaOt-Bu (9.87 g, 102.7 mmol), toluene (330 mL) were added, and stirred at 100° C. After the reaction was completed, the reaction mixture was extracted with CH₂Cl₂ and water. The organic layer was dried over MgSO₄ and concentrated. The resulting compound was separated by silicagel column chromatography and recrystallized to obtain 11.3 g of Product 1-1′. (yield: 77%)

Synthesis 1-4′

In a round bottom flask, bis(4-(naphthalen-1-yl)phenyl)amine (10 g, 23.7 mmol), 1-(4-bromophenyl)naphthalene (7.4 g, 26.1 mmol), Pd₂(dba)₃ (1.09 g, 1.19 mmol), P(t-Bu)₃ (0.5 g, 2.4 mmol), NaOt-Bu (7.52 g, 78.3 mmol), toluene (250 mL) were tested in the same manner as in the above 1-1′ to obtain 11.5 g of Product 1-4′. (Yield: 78%).

Synthesis 1-10′

In a round bottom flask, N-([1,1′-biphenyl]-4-yl)-[1,1′: 3′,1″-terphenyl]-5′-amine (10 g, 25.2 mmol), 5′-bromo-1,1′: 3′,1″-terphenyl (8.56 g, 27.7 mmol), Pd₂(dba)₃ (1.15 g, 1.26 mmol), P(t-Bu)₃ (0.51 g, 2.52 mmol), NaOt-Bu (7.98 g, 83.02 mmol), toluene (264 mL) were tested in the same manner as in the above 1-1′ to obtain 11.8 g of Product 1-10′. (Yield: 75%).

Synthesis 1-19′

In a round bottom flask, N-([1,1′-biphenyl]-4-yl)naphthalen-1-amine (10 g, 33.6 mmol), 2-bromodibenzo[b,d]thiophene (9.8 g, 37.2 mmol), Pd₂(dba)₃ (1.55 g, 1.7 mmol), P(t-Bu)₃ (0.68 g, 3.38 mmol), NaOt-Bu (10.76 g, 112 mmol), toluene (355 mL) were tested in the same manner as in the above 1-1′ to obtain 12.3 g of Product 1-19′. (Yield: 76%).

Synthesis 1-20′

In a round bottom flask, di([1,1′-biphenyl]-3-yl)amine (10 g, 31.1 mmol), 2-bromodibenzo[b,d]thiophene (9 g, 34.2 mmol), Pd₂(dba)₃ (1.42 g, 1.56 mmol), P(t-Bu)₃ (0.63 g, 3.11 mmol), NaOt-Bu (9.87 g, 102.7 mmol), toluene (327 mL) were tested in the same manner as in the above 1-1′ to obtain 12.2 g of Product 1-20′. (Yield: 78%).

Synthesis 1-23′

In a round bottom flask, N-(naphthalen-1-yl)-9,9-diphenyl-9H-fluoren-2-amine (10 g, 21.8 mmol), 2-bromodibenzo[b,d]thiophene (6.3 g, 23.9 mmol), Pd₂(dba)₃ (1 g, 1.09 mmol), P(t-Bu)₃ (0.44 g, 2.2 mmol), NaOt-Bu (6.9 g, 71.8 mmol), toluene (230 mL) were tested in the same manner as in the above 1-1′ to obtain 10.2 g of Product 1-23′. (Yield: 73%).

Synthesis 1-24′

In a round bottom flask, N-([1,1′-biphenyl]-4-yl)-9,9′-spirobi[fluoren]-2-amine (10 g, 20.7 mmol), 2-bromodibenzo[b,d]thiophene (6 g, 22.7 mmol), Pd₂(dba)₃ (0.95 g, 1.03 mmol), P(t-Bu)₃ (0.42 g, 2.07 mmol), NaOt-Bu (6.55 g, 68.2 mmol), toluene (220 mL) were tested in the same manner as in the above 1-1′ to obtain 10.2 g of Product 1-24′. (Yield: 74%).

Synthesis 1-29′

In a round bottom flask, N-(naphthalen-1-yl)dibenzo[b,d]thiophen-2-amine (10 g, 30.7 mmol), 2-(4-bromophenyl)dibenzo[b,d]thiophene (11.5 g, 33.8 mmol), Pd₂(dba)₃ (1.41 g, 1.54 mmol), P(t-Bu)₃ (0.62 g, 3.07 mmol), NaOt-Bu (9.75 g, 101.4 mmol), toluene (325 mL) were tested in the same manner as in the above 1-1′ to obtain 12.9 g of Product 1-29′. (Yield: 72%).

Synthesis 1-30′

In a round bottom flask, N-([1,1′-biphenyl]-4-yl)-[1,1′-biphenyl]-3-amine (10 g, 31.1 mmol), 2-(3-bromophenyl)dibenzo[b,d]thiophene (11.6 g, 34.2 mmol), Pd₂(dba)₃ (1.42 g, 1.55 mmol), P(t-Bu)₃ (0.63 g, 3.11 mmol), NaOt-Bu (9.9 g, 103 mmol), toluene (330 mL) were tested in the same manner as in the above 1-1′ to obtain 12.8 g of Product 1-30′. (Yield: 71%).

Synthesis 1-36′

In a round bottom flask, bis(dibenzo[b,d]thiophen-2-yl)amine (10 g, 26.2 mmol), 2-bromodibenzo[b,d]thiophene (7.59 g, 28.8 mmol), Pd₂(dba)₃ (1.2 g, 1.31 mmol), P(t-Bu)₃ (0.53 g, 2.62 mmol), NaOt-Bu (8.31 g, 86.5 mmol), toluene (275 mL) were tested in the same manner as in the above 1-1′ to obtain 11.4 g of Product 1-36′. (Yield: 77%).

Synthesis 1-49′

In a round bottom flask, di([1,1′-biphenyl]-4-yl)amine (10 g, 31.1 mmol), 2-(3-bromophenyl)dibenzo[b,d]furan (11.1 g, 34.2 mmol), Pd₂(dba)₃ (1.42 g, 1.56 mmol), P(t-Bu)₃ (0.63 g, 3.11 mmol), NaOt-Bu (9.9 g, 103 mmol), toluene (330 mL) were tested in the same manner as in the above 1-1′ to obtain 13.3 g of Product 1-49′. (Yield: 76%).

Synthesis 1-51′

In a round bottom flask, N-(4-(naphthalen-1-yl)phenyl)naphthalen-2-amine (10 g, 28.9 mmol), 2-(7-bromo-9,9-dimethyl-9H-fluoren-2-yl)dibenzo[b,d]furan (14 g, 32 mmol), Pd₂(dba)₃ (1.33 g, 1.45 mmol), P(t-Bu)₃ (0.59 g, 2.9 mmol), NaOt-Bu (9.2 g, 95.5 mmol), toluene (310 mL) were tested in the same manner as in the above 1-1′ to obtain 14.5 g of Product 1-51′. (Yield: 71%).

Synthesis 1-59′

In a round bottom flask, N-([1,1′-biphenyl]-4-yl)benzo[4,5]thieno[3,2-d]pyrimidin-2-amine (10 g, 28.3 mmol), 4-(4-bromophenyl)dibenzo[b,d]furan (10.1 g, 31.1 mmol), Pd₂(dba)₃ (1.3 g, 1.41 mmol), P(t-Bu)₃ (0.57 g, 2.83 mmol), NaOt-Bu (8.98 g, 93.4 mmol), toluene (300 mL) were tested in the same manner as in the above 1-1′ to obtain 12.3 g of Product 1-59′. (Yield: 73%).

Synthesis 1-71′

In a round bottom flask, di([1,1′-biphenyl]-4-yl)amine (10 g, 31.1 mmol), 2-(4-bromophenyl)-9,9′-spirobi[fluorene] (16.1 g, 34.2 mmol), Pd₂(dba)₃ (1.42 g, 1.56 mmol), P(t-Bu)₃ (0.63 g, 3.11 mmol), NaOt-Bu (9.87 g, 102.7 mmol), toluene (330 mL) were tested in the same manner as in the above 1-1′ to obtain 15.5 g of Product 1-71′. (Yield: 70%).

Synthesis 1-75′

In a round bottom flask, N-(4-(9,9-diphenyl-9H-fluoren-2-yl)phenyl)-[1,1′-biphenyl]-4-amine (10 g, 17.8 mmol), 3-bromo-9,9-diphenyl-9H-fluorene (7.78 g, 19.6 mmol), Pd₂(dba)₃ (0.82 g, 0.89 mmol), P(t-Bu)₃ (0.36 g, 1.78 mmol), NaOt-Bu (5.65 g, 58.75 mmol), toluene (190 mL) were tested in the same manner as in the above 1-1′ to obtain 11.3 g of Product 1-75′. (Yield: 72%).

TABLE 2 compound FD-MS compound FD-MS 1-1′ m/z = 473.21 (C₃₆H₂₇N = 473.61) 1-2′ m/z = 523.23 (C₄₀H₂₉N = 523.66) 1-3′ m/z = 573.25 (C₄₄H₃₁N = 573.72) 1-4′ m/z = 623.26 (C₄₈H₃₃N = 623.78) 1-5′ m/z = 447.20 (C₃₄H₂₅N = 447.57) 1-6′ m/z = 371.17 (C₂₈H₂₁N = 371.47) 1-7′ m/z = 471.20 (C₃₆H₂₅N = 471.59) 1-8′ m/z = 521.21 (C₄₀H₂₇N = 521.65) 1-9′ m/z = 549.25 (C₄₂H₃₁N = 549.70) 1-10′ m/z = 625.28 (C₄₈H₃₅N = 625.80) 1-11′ m/z = 675.29 (C₅₂H₃₇N = 675.86) 1-12′ m/z = 473.21 (C₃₆H₂₇N = 473.61) 1-13′ m/z = 523.23 (C₄₀H₂₉N = 523.66) 1-14′ m/z = 623.26 (C₄₈H₃₃N = 623.78) 1-15′ m/z = 549.25 (C₄₂H₃₁N = 549.70) 1-16′ m/z = 625.28 (C₄₈H₃₅N = 625.80) 1-17′ m/z = 503.17 (C₃₆H₂₅NS = 503.66) 1-18′ m/z = 603.20 (C₄₄H₂₉NS = 603.77) 1-19′ m/z = 477.16 (C₃₄H₂₃NS = 477.62) 1-20′ m/z = 503.17 (C₃₆H₂₅NS = 503.66) 1-21′ m/z = 451.14 (C₃₂H₂₁NS = 451.58) 1-22′ m/z = 593.22 (C₄₃H₃₁NS = 593.78) 1-23′ m/z = 641.22 (C₄₇H₃₁NS = 641.82) 1-24′ m/z = 665.22 (C₄₉H₃₁NS = 665.84) 1-25′ m/z = 503.17 (C₃₆H₂₅NS = 503.66) 1-26′ m/z = 655.23 (C₄₈H₃₃NS = 655.85) 1-27′ m/z = 695.26 (C₅₁H₃₇NS = 695.91) 1-28′ m/z = 593.18 (C₄₂H₂₇NOS = 593.73) 1-29′ m/z = 583.14 (C₄₀H₂₅NS₂ = 583.76) 1-30′ m/z = 579.20 (C₄₂H₂₉NS = 579.75) 1-31′ m/z = 685.19 (C₄₈H₃₁NS₂ = 685.90) 1-32′ m/z = 719.23 (C₅₂H₃₃NOS = 719.89) 1-33′ m/z = 629.22 (C₄₆H₃₁NS = 629.81) 1-34′ m/z = 629.22 (C₄₆H₃₁NS = 629.81) 1-35′ m/z = 603.20 (C₄₄H₂₉NS = 603.77) 1-36′ m/z = 563.08 (C₃₆H₂₁NS₃ = 563.75) 1-37′ m/z = 639.11 (C₄₂H₂₅NS₃ = 639.85) 1-38′ m/z = 715.15 (C₄₈H₂₉NS₃ = 715.95) 1-39′ m/z = 791.18 (C₅₄H₃₃NS₃ = 792.04) 1-40′ m/z = 607.16 (C₄₂H₂₅NO₂S = 607.72) 1-41′ m/z = 633.21 (C₄₅H₃₁NOS = 633.80) 1-42′ m/z = 733.24 (C₅₃H₃₅NOS = 733.92) 1-43′ m/z = 883.29 (C₆₅H₄₁NOS = 884.09) 1-44′ m/z = 585.13 (C₃₈H₂₃N₃S₂ = 585.74) 1-45′ m/z = 553.19 (C₄₀H₂₇NS = 553.71) 1-46′ m/z = 603.20 (C₄₄H₂₉NS = 603.77) 1-47′ m/z = 841.28 (C₆₃H₃₉NS = 842.06) 1-48′ m/z = 563.22 (C₄₂H₂₉NO = 563.69) 1-49′ m/z = 563.22 (C₄₂H₂₉NO = 563.69) 1-50′ m/z = 613.24 (C₄₆H₃₁NO = 613.76) 1-51′ m/z = 703.29 (C₅₃H₃₇NO = 703.87) 1-52′ m/z = 587.22 (C₄₄H₂₉NO = 587.71) 1-53′ m/z = 639.26 (C₄₈H₃₃NO = 639.78) 1-54′ m/z = 639.26 (C₄₈H₃₃NO = 639.78) 1-55′ m/z = 653.24 (C₄₈H₃₁NO₂ = 653.77) 1-56′ m/z = 603.26 (C₄₅H₃₃NO = 603.75) 1-57′ m/z = 727.29 (C₅₅H₃₇NO = 727.89) 1-58′ m/z = 725.27 (C₅₅H₃₅NO = 725.87) 1-59′ m/z = 595.17 (C₄₀H₂₅N₃OS = 595.71) 1-60′ m/z = 567.26 (C₄₂H₃₃NO = 567.72) 1-61′ m/z = 611.22 (C₄₆H₂₉NO = 611.73) 1-62′ m/z = 617.18 (C₄₄H₂₇NOS = 617.76) 1-63′ m/z = 637.24 (C₄₈H₃₁NO = 637.77) 1-64′ m/z = 667.21 (C₄₈H₂₉NO₃ = 667.75) 1-65′ m/z = 767.25 (C₅₆H₃₃NO₃ = 767.87) 1-66′ m/z = 681.27 (C₅₀H₃₅NO₂ = 681.82) 1-67′ m/z = 658.22 (C₄₅H₃₀N₄S = 658.82) 1-68′ m/z = 655.23 (C₄₈H₃₃NS = 655.86) 1-69′ m/z = 744.26 (C₅₄H₃₆N₂S = 744.96) 1-70′ m/z = 784.27 (C₅₅H₃₆N₄S = 784.98) 1-71′ m/z = 553.19 (C₄₀H₂₇NS = 553.72) 1-72′ m/z = 553.19 (C₄₀H₂₇NS = 553.72) 1-73′ m/z = 543.20 (C₃₉H₂₉NS = 543.73) 1-74′ m/z = 671.21 (C₄₈H₃₀FNS = 671.83) 1-75′ m/z = 641.25 (C₄₆H₃₁N₃O = 641.77) 1-76′ m/z = 639.26 (C₄₈H₃₃NO = 639.80) 1-77′ m/z = 652.25 (C₄₈H₃₂N₂O = 652.80) 1-78′ m/z = 614.24 (C₄₅H₃₀N₂O = 614.75) 1-79′ m/z = 587.22 (C₄₄H₂₉NO = 587.72) 1-80′ m/z = 613.24 (C₄₆H₃₁NO = 613.76) 1-81′ m/z = 543.26 (C₄₀H₃₃NO = 543.71) 1-82′ m/z = 667.25 (C₄₉H₃₃NO₂ = 667.81)

Synthesis Examples 2

The final product 2 represented by Formula (2) of the present invention is prepared by reacting Sub 3 and Sub 4 as shown in the following Reaction Scheme 3.

Synthesis Example of Sub 3

Sub 3 of Reaction Scheme 4 can be synthesized by the reaction path of the following Reaction Scheme 4, but is not limited thereto.

Synthesis Examples of Sub 3 (1)

After 5-bromobenzo[b]naphtha[1,2-d]thiophene (50 g, 155 mmol), bis(pinacolato)diboron (43.4 g, 171 mmol), KOAc (46 g, 466 mmol), PdCl₂(dppf) (3.8 g, 4.7 mmol) were dissolved in DMF (980 mL), and refluxed at 120° C. for 12 hours. When the reaction was completed, the temperature of the reaction was cooled to room temperature, extracted with CH₂Cl₂ and wiped with water. The organic layer was dried over MgSO₄ and concentrated. The resulting compound was recrystallized by CH₂Cl₂ and methanol solvent to obtain Sub 3-2-1 (45 g, 80%).

Synthesis Method of Sub 3-4-1

Sub 3-2-1 (40 g, 111 mmol), bromo-2-nitrobenzene (26.91 g, 133 mmol), K₂CO₃ (46.03 g, 333 mmol), Pd(PPh₃)₄ (7.7 g, 6.66 mmol) were added in a round bottom flask and THF (490 mL) and water (245 mL) were added to dissolve and refluxed at 80° C. for 12 hours. When the reaction was completed, the temperature of the reaction was cooled to room temperature, extracted with CH₂Cl₂ and wiped with water. The organic layer was dried over MgSO₄ and concentrated. The resulting compound was separated by silicagel column chromatography to obtain Sub 3-4-1 (27.6 g, 70%).

Synthesis Method of Sub 3 (1)

Sub 3-4-1 (20 g, 56.3 mmol) and triphenylphosphine (37 g, 141 mmol) were dissolved in o-dichlorobenzene (235 mL) and refluxed for 24 hours. When the reaction was completed, the solvent was removed using reduced pressure distillation. The resulting compound was separated by silicagel column chromatography and recrystallized to obtain Sub 3 (1) (13.6 g, 75%).

Synthesis Example of Sub 3 (2)

Synthesis Method of Sub 3-2-2

5-bromobenzo[b]naphtho[2,1-d]thiophene (50 g, 160 mmol), bis(pinacolato)diboron (44.6 g, 176 mmol), KOAc (47 g, 479 mmol), PdCl₂(dppf) (3.91 g, 4.8 mmol), DMF (IL) were carried out in the same manner as in Sub 3-2-1 to give the product Sub 3-2-2 (45 g, 78%).

Synthesis Method of Sub 3-4-2

Sub 3-2-2 (40 g, 111 mmol), bromo-2-nitrobenzene (26.91 g, 133 mmol), K₂CO₃ (46.03 g, 333 mmol), Pd(PPh₃)₄ (7.7 g, 6.7 mmol), THF (490 mL) and water (245 mL) were carried out in the same manner as in Sub 3-4-1 to give the product Sub 3-4-2 (25.6 g, 65%).

Synthesis Method of Sub 3 (2)

Sub 3-4-2 (20 g, 56.3 mmol), triphenylphosphine (44.28 g, 0.17 mol), o-dichlorobenzene (235 mL) was carried out in the same manner as in Sub 3 (1) to give the product Sub 3 (2) (12 g, 66%).

Synthesis Example of Sub 3 (7)

Synthesis Method of Sub 3-2-3

9-bromo-11-phenyl-11H-benzo[a]carbazole (50 g, 134 mmol), bis(pinacolato)diboron (37.5 g, 148 mmol), KOAc (40 g, 403 mmol), PdCl₂(dppf) (3.3 g, 4.0 mmol) was carried out in the same manner as in Sub 3-2-1 to give the product Sub 3-2-3 (45.1 g, 80%).

Synthesis Method of Sub 3-4-3

Sub 3-2-3 (46.1 g, 111 mmol), Sub 3-3 (26.7 g, 131 mmol), K₂CO₃ (45.6 g, 330 mmol), Pd(PPh₃)₄ (7.63 g, 6.6 mmol) were carried out in the same manner as in Sub 3-4-1 to give the product Sub 3-4-3 (29.6 g, 65%).

Synthesis Method of Sub 3 (7)

Sub 3-4-3 (20.7 g, 50 mmol), triphenylphosphine (32.7 g, 125 mmol), o-dichlorobenzene (205 mL) were carried out in the same manner as in Sub 3 (1) to give the product Sub 3 (7) (13.0 g, 68%).

Synthesis Example of Sub 3 (13)

Synthesis Method of Sub 3-2-4

Sub 3-1-4 (55.6 g, 160 mmol), bis(pinacolato)diboron (44.7 g, 176 mmol), KOAc (47.1 g, 480 mmol), PdCl₂(dppf) (3.92 g, 4.8 mmol) were carried out in the same manner as in Sub 3-2-1 to give the product Sub 3-2-4 (47.9 g, 76%).

Synthesis Method of Sub 3-4-4

Sub 3-2-4 (43.4 g, 110 mmol), Sub 3-3 (26.7 g, 132 mmol), K₂CO₃ (45.6 g, 330 mmol), Pd(PPh₃)₄ (7.63 g, 6.6 mmol) were carried out in the same manner as in Sub 3-4-1 to give the product Sub 3-4-4 (27.4 g, 64%).

Synthesis Method of Sub 3 (13)

Sub 3-4-4 (19.5 g, 50.1 mmol), triphenylphosphine (32.8 g, 125.2 mmol), o-dichlorobenzene (205 mL) were carried out in the same manner as in Sub 3 (1) to give the product Sub 3 (13) (11.5 g, 64%).

Synthesis Example of Sub 3 (26)

Synthesis Method of Sub 3-2-5

Sub 3-1-5 (51.7 g, 160 mmol), bis(pinacolato)diboron (44.7 g, 176 mmol), KOAc (47.1 g, 480 mmol), PdCl₂(dppf) (3.92 g, 4.8 mmol) were carried out in the same manner as in Sub 3-2-1 to give the product Sub 3-2-5 (46.2 g, 78%).

Synthesis Method of Sub 3-4-5

Sub 3-2-5 (40.7 g, 110 mmol), Sub 3-3-1 (33.2 g, 132 mmol), K₂CO₃ (45.6 g, 330 mmol), Pd(PPh₃)₄ (7.62 g, 6.6 mmol) were carried out in the same manner as in Sub 3-4-1 to give the product Sub 3-4-5 (30.6 g, 67%).

Synthesis Method of Sub 3 (26)

Sub 3-4-5 (20.8 g, 50.1 mmol), triphenylphosphine (32.8 g, 125 mmol), o-dichlorobenzene (205 mL) were carried out in the same manner as in Sub 3 (1) to give the product Sub 3 (26) (11.9 g, 62%).

Synthesis Example of Sub 3 (39)

Synthesis Method of Sub 3-2-6

Sub 3-1-6 (59.6 g, 160 mmol), bis(pinacolato)diboron (44.7 g, 176 mmol), KOAc (47.1 g, 480 mmol), PdCl₂(dppf) (3.92 g, 4.8 mmol) were carried out in the same manner as in Sub 3-2-1 to give the product Sub 3-2-6 (50.4 g, 75%).

Synthesis Method of Sub 3-4-6

Sub 3-2-6 (46.1 g, 110 mmol), Sub 3-3-2 (33.3 g, 132 mmol), K₂CO₃ (45.6 g, 330 mmol), Pd(PPh₃)₄ (7.63 g, 6.6 mmol) were carried out in the same manner as in Sub 3-4-1 to give the product Sub 3-4-6 (32.2 g, 63%).

Synthesis Method of Sub 3 (39)

Sub 3-4-6 (23.2 g, 50 mmol), triphenylphosphine (32.7 g, 125 mmol), o-dichlorobenzene (205 mL) were carried out in the same manner as in Sub 3 (1) to give the product Sub 3 (39) (14.1 g, 65%).

Synthesis Example of Sub 3 (45)

Synthesis Method of Sub 3-2-7

Sub 3-1-7 (47.5 g, 160 mmol), bis(pinacolato)diboron (44.7 g, 176 mmol), KOAc (47.1 g, 480 mmol), PdCl₂(dppf) (3.92 g, 4.8 mmol) were carried out in the same manner as in Sub 3-2-1 to give the product Sub 3-2-7 (43.0 g, 78%).

Synthesis Method of Sub 3-4-7

Sub 3-2-7 (37.9 g, 110 mmol), Sub 3-3-1 (33.3 g, 132 mmol), K₂CO₃ (45.7 g, 330 mmol), Pd(PPh₃)₄ (7.64 g, 6.6 mmol) were carried out in the same manner as in Sub 3-4-1 to give the product Sub 3-4-7 (27.4 g, 64%).

Synthesis Method of Sub 3 (45)

Sub 3-4-7 (19.5 g, 50.1 mmol), triphenylphosphine (32.8 g, 125 mmol), o-dichlorobenzene (205 mL) were carried out in the same manner as in Sub 3 (1) to give the product Sub 3 (45) (12.0 g, 67%).

Synthesis Example of Sub 3 (66)

Synthesis Method of Sub 3-2-8

Sub 3-1-8 (43.7 g, 160 mmol), bis(pinacolato)diboron (44.7 g, 176 mmol), KOAc (47.1 g, 480 mmol), PdCl₂(dppf) (3.9 g, 4.8 mmol) were carried out in the same manner as in Sub 3-2-1 to give the product Sub 3-2-8. (38.4 g, 75%).

Synthesis Method of Sub 3-4-8

Sub 3-2-8 (35.2 g, 110 mmol), Sub 3-3-3 (39.9 g, 132 mmol), K₂CO₃ (45.6 g, 330 mmol), Pd(PPh₃)₄ (7.6 g, 6.6 mmol) were carried out in the same manner as in Sub 3-4-1 to give the product Sub 3-4-8 (31.5 g, 69%).

Synthesis Method of Sub 3 (66)

Sub 3-4-8 (20.8 g, 50 mmol), triphenylphosphine (32.8 g, 125 mmol), o-dichlorobenzene (205 mL) were carried out in the same manner as in Sub 3 (1) to give the product Sub 3 (66) (12.5 g, 65%).

Synthesis Example of Sub 3 (67)

Synthesis Method of Sub 3-2-9

Sub 3-1-9 (70 g, 192.69 mmol), DMF (1214 ml), Bis(pinacolato)diboron (53.83 g, 211.96 mmol), Pd(dppf)Cl₂ (4.23 g, 5.78 mmol), KOAc (56.73 g, 578.08 mmol) were carried out in the same manner as in Sub 3-2-1 to give the product. (64.05 g, 81%).

Synthesis Method of Sub 3-4-9

Sub 3-2-9 (63.2 g, 154.02 mmol), THF (216 ml), 1-bromo-2-nitrobenzene (34.22 g, 169.42 mmol), Pd(PPh₃)₄ (4.23 g, 4.62 mmol), K₂CO₃ (44.40 g, 462.06 mmol), water (108 ml) were carried out in the same manner as in Sub 3-4-1 to give the product. (45.59 g, 73%).

Synthesis Method of Sub 3 (67)

Sub 3-4-9 (45.50 g, 112.22 mmol), o-dichlorobenzene (224 ml), triphenylphosphine (88.30 g, 336.65 mmol) were carried out in the same manner as in Sub 3 (1) to give the product. (31.85 g, 76%).

Synthesis Example of Sub 3 (72)

(1) Synthesis of Sub 3-4-10

Sub 3-2-9 (41 g, 99.92 mmol), 2-(3-bromo-4-nitrophenyl)-9-phenyl-9H-carbazole (44.29 g, 99.92 mmol), Pd(PPh₃)₄ (3.46 g, 3.00 mmol), K₂CO₃ (41.43 g, 299.75 mmol), THF (440 ml), water (220 ml) were carried out in the same manner as in Sub 3-4-1 to give the product. (47.82 g, 74%).

(2) Synthesis of Sub 3 (72)

Sub 3-4-10 (47 g, 72.67 mmol), triphenylphosphine (57.18 g, 218.01 mmol), o-dichlorobenzene (145 ml) were carried out in the same manner as in Sub 3 (1) to give the product. (28.15 g, 63%).

Synthesis Example of Sub 3 (74)

1) Synthesis of S-I-1

(4-bromo-6-(dibenzo[b,d]furan-2-yl)naphthalen-1-yl)boronic acid (100 g, 239.77 mmol) was dissolved in THF (1055 ml) in a round bottom flask, and 2-iodonaphthalen-1-ol (64.75 g, 239.77 mmol), Pd(PPh)₄ (4.16 g, 3.60 mmol), NaOH (14.39 g, 359.65 mmol), water (527 ml) were added and stirred at 80° C. After the reaction was completed, the reaction mixture was extracted with CH₂Cl₂ and water. The organic layer was dried over MgSO₄ and concentrated. The resulting compound was separated by silicagel column chromatography and recrystallized to obtain 86.51 g of the product. (yield: 70%)

2) Synthesis of Sub 3-1-10

The starting material, S-I-1 (86 g, 166.86 mmol) was placed in a round bottom flask with Pd(OAc)₂ (3.75 g, 16.69 mmol) and 3-nitropyridine (2.07 g, 16.69 mmol) and dissolved in C₆F₆ (250 ml) and DMI (167 ml), followed by addition of tert-butyl peroxybenzoate (64.82 g, 333.71 mmol) and stirring at 90° C. After the reaction was completed, the reaction mixture was extracted with CH₂Cl₂ and water. The organic layer was dried over MgSO₄ and concentrated. The resulting compound was separated by silicagel column chromatography and recrystallized to obtain 62.53 g of the product. (yield: 73%)

3) Synthesis of Sub 3-2-10

3-1-10 (62.50 g, 121.74 mmol), DMF (609 ml), Bis(pinacolato)diboron (34.01 g, 133.91 mmol), Pd(dppf)Cl₂ (2.67 g, 3.65 mmol), KOAc (35.84 g, 365.22 mmol) were carried out in the same manner as in Sub 3-2-1 to give the product. (51.86 g, 76%).

4) Synthesis of Sub 3-4-11

Sub 3-2-10 (51.8 g, 92.42 mmol), 1-bromo-2-nitrobenzene (18.67 g, 92.42 mmol), Pd(PPh₃)₄ (3.2 g, 2.77 mmol), K₂CO₃ (38.32 g, 277.27 mmol), THF (407 ml), water (203 ml) were carried out in the same manner as in Sub 3-4-1 to give the product. (43.13 g, 84%).

5) Synthesis of Sub 3 (74)

Sub 3-4-11 (43 g, 77.4 mmol), triphenylphosphine (60.9 g, 232.19 mmol), o-dichlorobenzene (155 ml) were carried out in the same manner as in Sub 3 (1) to give the product. (31.61 g, 78%).

Synthesis Example of Sub 3 (75)

1) Synthesis of S-I-2

(4-chloronaphthalen-1-yl)boronic acid (31.07 g, 150.5 mmol), THF (662 ml), 3-bromo-6-(dibenzo[b,d]thiophen-3-yl)naphthalen-2-ol (61 g, 150.5 mmol), Pd(PPh₃)₄ (2.61 g, 2.26 mmol), NaOH (9.03 g, 225.75 mmol), water (331 ml) were carried out in the same manner as in Sub S-I-1 to give the product. (51.31 g, 70%).

2) Synthesis of Sub 3-1-11

S-I-2 (51 g, 104.72 mmol) was placed in a round bottom flask with Pd(OAc)₂ (2.35 g, 10.47 mmol) and 3-nitropyridine (1.30 g, 10.47 mmol) were added and dissolved in C₆F₆ (157.1 ml) and DMI (104 ml), and tert-butyl peroxybenzoate (40.68 g, 209.44 mmol) was carried out in the same manner as in Sub 3-1-10 to give the product. (36.57 g, 72%).

3) Synthesis of Sub 3-2-11

3-1-11 (36 g, 74.23 mmol), DMF (371 ml), Bis(pinacolato)diboron (20.73 g, 81.65 mmol), Pd(dppf)Cl₂ (1.63 g, 2.23 mmol), KOAc (21.85 g, 222.68 mmol) were carried out in the same manner as in Sub 3-2-1 to give the product. (34.23 g, 80%).

4) Synthesis of Sub 3-4-12

Sub 3-2-11 (34 g, 58.97 mmol), 1-bromo-2-nitrobenzene (11.91 g, 58.97 mmol), Pd(PPh₃)₄ (2.04 g, 1.77 mmol), K₂CO₃ (24.45 g, 176.92 mmol), THF (259 ml), water (129 ml) were carried out in the same manner as in Sub 3-4-1 to give the product. (27.64 g, 82%).

5) Synthesis of Sub 3 (75)

Sub 3-4-12 (27.5 g, 48.11 mmol), triphenylphosphine (37.85 g, 144.32 mmol), o-dichlorobenzene (96 ml) were carried out in the same manner as in Sub 3 (1) to give the product. (20.25 g, 78%).

Synthesis Example of Sub 3 (76)

1) Synthesis of Sub 3-2-12

Sub 3-1-12 (20 g, 57.60 mmol), DMF (288 ml), Bis(pinacolato)diboron (16.09 g, 63.36 mmol), Pd(dppf)Cl₂ (1.26 g, 1.73 mmol), KOAc (16.96 g, 172.81 mmol) were carried out in the same manner as in Sub 3-2-1 to give the product. (17.94 g, 79%).

2) Synthesis of Sub 3-4-13

Sub 3-2-12 (17 g, 43.12 mmol), 3-bromo-4-nitro-1,1′-biphenyl (11.99 g, 43.12 mmol), Pd(PPh₃)₄ (1.49 g, 1.29 mmol), K₂CO₃ (17.88 g, 129.35 mmol), THF (189 ml), water (94 ml) were carried out in the same manner as in Sub 3-4-1 to give the product. (15.45 g, 77%).

3) Synthesis of Sub 3 (76)

Sub 3-2-12 (15 g, 32.22 mmol), triphenylphosphine (25.36 g, 96.67 mmol), o-dichlorobenzene (64 ml) were carried out in the same manner as in Sub 3 (1) to give the product. (11.73 g, 84%).

Examples of Sub 3 include, but are not limited to, the followings.

TABLE 3 compound FD-MS compound FD-MS Sub 3 (1) m/z = 323.08 (C₂₂H₁₃NS = 323.41) Sub 3 (2) m/z = 323.08 (C₂₂H₁₃NS = 323.41) Sub 3 (3) m/z = 307.10 (C₂₂H₁₃NO = 307.34) Sub 3 (4) m/z = 307.10 (C₂₂H₁₃NO = 307.34) Sub 3 (5) m/z = 333.15 (C₂₅H₁₉N = 333.43) Sub 3 (6) m/z = 382.15 (C₂₈H₁₈N₂ = 382.46) Sub 3 (7) m/z = 382.15 (C₂₈H₁₈N₂ = 382.47) Sub 3 (8) m/z = 323.08 (C₂₂H₁₃NS = 323.41) Sub 3 (9) m/z = 307.10 (C₂₂H₁₃NO = 307.35) Sub 3 (10) m/z = 383.17 (C₂₉H₂₁N = 383.49) Sub 3 (11) m/z = 373.09 (C₂₆H₁₅NS = 373.47) Sub 3 (12) m/z = 323.08 (C₂₂H₁₃NS = 323.41) Sub 3 (13) m/z = 357.12 (C₂₆H₁₅NO = 357.41) Sub 3 (14) m/z = 333.15 (C₂₅H₁₉N = 333.43) Sub 3 (15) m/z = 373.09 (C₂₆H₁₅NS = 373.47) Sub 3 (16) m/z = 357.12 (C₂₆H₁₅NO = 357.41) Sub 3 (17) m/z = 383.17 (C₂₉H₂₁N = 383.49) Sub 3 (18) m/z = 373.09 (C₂₆H₁₅NS = 373.47) Sub 3 (19) m/z = 407.13 (C₃₀H₁₇NO = 407.47) Sub 3 (20) m/z = 433.18 (C₃₃H₂₃N = 433.55) Sub 3 (21) m/z = 373.09 (C₂₆H₁₅NS = 373.47) Sub 3 (22) m/z = 357.12 (C₂₆H₁₅NO = 357.41) Sub 3 (23) m/z = 662.25 (C₄₈H₃₀N₄ = 662.80) Sub 3 (24) m/z = 373.09 (C₂₆H₁₅NS = 373.47) Sub 3 (25) m/z = 357.12 (C₂₆H₁₅NO = 357.41) Sub 3 (26) m/z = 383.17 (C₂₉H₂₁N = 383.49) Sub 3 (27) m/z = 432.16 (C₃₂H₂₀N₂ = 432.53) Sub 3 (28) m/z = 323.08 (C₂₂H₁₃NS = 323.41) Sub 3 (29) m/z = 307.10 (C₂₂H₁₃NO = 307.35) Sub 3 (30) m/z = 455.17 (C₃₅H₂₁N = 455.56) Sub 3 (31) m/z = 432.16 (C₃₂H₂₀N₂ = 432.53) Sub 3 (32) m/z = 323.08 (C₂₂H₁₃NS = 323.41) Sub 3 (33) m/z = 307.10 (C₂₂H₁₃NO = 307.35) Sub 3 (34) m/z = 383.17 (C₂₉H₂₁N = 383.49) Sub 3 (35) m/z = 432.16 (C₃₂H₂₀N₂ = 439.53) Sub 3 (36) m/z = 373.09 (C₂₆H₁₅NS = 373.47) Sub 3 (37) m/z = 357.12 (C₂₆H₁₅NO = 357.41) Sub 3 (38) m/z = 383.17 (C₂₉H₂₁N = 383.49) Sub 3 (39) m/z = 432.16 (C₃₂H₂₀N₂ = 432.53) Sub 3 (40) m/z = 373.09 (C₂₆H₁₅NS = 373.47) Sub 3 (41) m/z = 357.12 (C₂₆H₁₅NO = 357.41) Sub 3 (42) m/z = 383.17 (C₂₉H₂₁N = 383.49) Sub 3 (43) m/z = 432.16 (C₃₂H₂₀N₂ = 432.53) Sub 3 (44) m/z = 373.09 (C₂₆H₁₅NS = 373.47) Sub 3 (45) m/z = 357.12 (C₂₆H₁₅NO = 357.41) Sub 3 (46) m/z = 505.18 (C₃₉H₂₃N = 505.62) Sub 3 (47) m/z = 382.15 (C₂₈H₁₈N₂ = 382.47) Sub 3 (48) m/z = 323.08 (C₂₂H₁₃NS = 323.41) Sub 3 (49) m/z = 307.10 (C₂₂H₁₃NO = 307.35) Sub 3 (50) m/z = 333.15 (C₂₅H₁₉N = 333.43) Sub 3 (51) m/z = 432.16 (C₃₂H₂₀N₂ = 432.53) Sub 3 (52) m/z = 323.08 (C₂₂H₁₃NS = 323.41) Sub 3 (53) m/z = 307.10 (C₂₂H₁₃NO = 307.35) Sub 3 (54) m/z = 457.18 (C₃₅H₂₃N = 457.58) Sub 3 (55) m/z = 432.16 (C₃₂H₂₀N₂ = 432.53) Sub 3 (56) m/z = 373.09 (C₂₆H₁₅NS = 373.47) Sub 3 (57) m/z = 357.12 (C₂₆H₁₅NO = 357.41) Sub 3 (58) m/z = 383.17 (C₂₉H₂₁N = 383.49) Sub 3 (59) m/z = 616.17 (C₄₂H₂₄N₄S = 616.74) Sub 3 (60) m/z = 323.08 (C₂₂H₁₃NS = 323.41) Sub 3 (61) m/z = 307.10 (C₂₂H₁₃NO = 307.35) Sub 3 (62) m/z = 373.09 (C₂₆H₁₅NS = 373.47) Sub 3 (63) m/z = 432.16 (C₃₂H₂₀N₂ = 432.53) Sub 3 (64) m/z = 373.09 (C₂₆H₁₅NS = 373.47) Sub 3 (65) m/z = 357.12 (C₂₆H₁₅NO = 357.41) Sub 3 (66) m/z = 383.17 (C₂₉H₂₁N = 383.49) Sub 3 (67) m/z = 373.09 (C₂₆H₁₅NS = 373.47) Sub 3 (68) m/z = 373.09 (C₂₆H₁₅NS = 373.47) Sub 3 (69) m/z = 357.12 (C₂₆H₁₅NO = 357.41) Sub 3 (70) m/z = 357.12 (C₂₆H₁₅NO = 357.41) Sub 3 (71) m/z = 357.12 (C₂₆H₁₅NO = 357.41) Sub 3 (72) m/z = 614.18 (C₄₄H₂₆N₂S = 614.77) Sub 3 (73) m/z = 423.11 (C₃₀H₁₇NS = 423.53) Sub 3 (74) m/z = 523.16 (C₃₈H₂₁NO₂ = 523.59) Sub 3 (75) m/z = 539.13 (C₃₈H₂₁NOS = 539.65) Sub 3 (76) m/z = 433.15C₃₂H₁₉NO = 433.51)

Examples of Sub 4

Examples of Sub 4 include, but are not limited to, the followings.

TABLE 4 compound FD-MS compound FD-MS Sub 4-1 m/z = 155.96 (C₆H₅Br = 157.01) Sub 4-2 m/z = 205.97 (C₁₀H₇Br = 207.07) Sub 4-3 m/z = 205.97 (C₁₀H₇Br = 207.07) Sub 4-4 m/z = 231.99 (C₁₂H₉Br = 233.10) Sub 4-5 m/z = 309.02 (C₁₇H₁₂BrN = 310.19) Sub 4-6 m/z = 311.01 (C₁₅H₁₀BrN₃ = 312.16) Sub 4-7 m/z = 310.01 (C₁₆H₁₁BrN₂ = 311.18) Sub 4-8 m/z = 310.01 (C₁₆H₁₁BrN₂ = 311.18) Sub 4-9 m/z = 310.01 (C₁₆H₁₁BrN₂ = 311.18) Sub 4-10 m/z = 387.04 (C₂₁H₁₄BrN₃ = 388.26) Sub 4-11 m/z = 386.04 (C₂₂H₁₅BrN₂ = 387.27) Sub 4-12 m/z = 386.04 (C₂₂H₁₅BrN₂ = 387.27) Sub 4-13 m/z = 348.03 (C₁₉H₁₃BrN₂ = 349.22) Sub 4-14 m/z = 271.99 (C₁₃H₉BrN₂ = 273.13) Sub 4-15 m/z = 283.99 (C₁₄H₉BrN₂ = 285.14) Sub 4-16 m/z = 374.01 (C₂₀H₁₁BrN₂O = 375.22) Sub 4-17 m/z = 400.06 (C₂₃H₁₇BrN₂ = 401.30) Sub 4-18 m/z = 360.03 (C₂₀H₁₃BrN₂ = 361.23) Sub 4-19 m/z = 476.09 (C₂₉H₂₁BrN₂ = 477.39) Sub 4-20 m/z = 284.99 (C₁₃H₈BrN₃ = 286.13) Sub 4-21 m/z = 289.03 (C₁₄H₄D₅BrN₂ = 290.2) Sub 4-22 m/z = 284.99 (C₁₃H₈BrN₃ = 286.13) Sub 4-23 m/z = 375.00 (C₁₉H₁₀BrN₃O = 376.2) Sub 4-24 m/z = 401.05 (C₂₂H₁₆BrN₃ = 402.29) Sub 4-25 m/z = 296.02 (C₁₆H₉ClN₂S = 296.77) Sub 4-26 m/z = 322.03 (C₁₈H₁₁ClN₂S = 322.81) Sub 4-27 m/z = 322.03 (C₁₈H₁₁ClN₂S = 322.81) Sub 4-28 m/z = 168.98 (C₇H₄ClNS = 169.63) Sub 4-29 m/z = 168.98 (C₇H₄ClNS = 169.63)) Sub 4-30 m/z = 169.97 (C₆H₃ClN₂S = 170.62) Sub 4-31 m/z = 246.00 (C₁₂H₇ClN₂S = 246.72) Sub 4-32 m/z = 322.03 (C₁₈H₁₁ClN₂S = 322.81) Sub 4-33 m/z = 322.03 (C₁₈H₁₁ClN₂S = 322.81) Sub 4-34 m/z = 168.98 (C₇H₄ClNS = 169.63) Sub 4-35 m/z = 168.98 (C₇H₄ClNS = 169.63)) Sub 4-36 m/z = 169.97 (C₆H₃ClN₂S = 170.62) Sub 4-37 m/z = 229.04 (C₁₂H₈ClN₃ = 229.67) Sub 4-38 m/z = 279.06 (C₁₆H₁₀ClN₃ = 279.72) Sub 4-39 m/z = 305.07 (C₁₈H₁₂ClN₃ = 305.76) Sub 4-40 m/z = 228.05 (C₁₃H₉ClN₂ = 228.68) Sub 4-41 m/z = 228.05 (C₁₃H₉ClN₂ = 228.68) Sub 4-42 m/z = 229.04 (C₁₂H₈ClN₃ = 229.67) Sub 4-43 m/z = 229.04 (C₁₂H₈ClN₃ = 229.67) Sub 4-44 m/z = 279.06 (C₁₆H₁₀ClN₃ = 279.72) Sub 4-45 m/z = 305.07 (C₁₈H₁₂ClN₃ = 305.76) Sub 4-46 m/z = 228.05 (C₁₃H₉ClN₂ = 228.68) Sub 4-47 m/z = 228.05 (C₁₃H₉ClN₂ = 228.68) Sub 4-48 m/z = 229.04 (C₁₂H₈ClN₃ = 229.67) Sub 4-49 m/z = 330.1 (C₂₀H₁₁ClN₂O = 330.77) Sub 4-50 m/z = 372.05 (C₂₂H₁₃ClN₂S = 372.87) Sub 4-51 m/z = 366.09 (C₂₄H₁₅ClN₂ = 366.85) Sub 4-52 m/z = 340.08 (C₂₂H₁₃ClN₂ = 340.81) Sub 4-53 m/z = 290.06 (C₁₈H₁₁ClN₂ = 290.75) Sub 4-54 m/z = 340.08 (C₂₂H₁₃ClN₂ = 340.81) Sub 4-55 (m/z = 240.05 (C₁₄H₉ClN₂ = 240.69)

Synthesis of Sub 5

If Ar⁴ of Final Product 2 in Reaction Scheme 3 is

Final Product 2 ‘can be synthesized by the following reaction path, but not limited thereto.

R^(c) is the same as R³, R⁴ and R⁵ defined above, one of R^(c)s are R^(c′), R^(c′) is any one selected from the group consisting of deuterium; halogen; a C₆-C₆₀ aryl group; a fluorenyl group; a C₂-C₆₀ heterocyclic group including at least one heteroatom of O, N, S, Si or P; a fused ring group of a C₃-C₆₀ aliphatic ring and a C₆-C₆₀ aromatic ring; a C₁-C₅₀ alkyl group; a C₂-C₂₀ alkenyl group; a C₂-C₂₀ alkynyl group; a C₁-C₃₀ alkoxyl group; a C₆-C₃₀ aryloxy group; and -L′-N(R_(a))(R_(b));

x is an integer of 0 to 10,

C ring is the same as A or B defined above.

Hal^(2′)=I, Br

Hal^(1′), Hal^(3′)=Cl, Br

In Reaction Scheme 6,

were synthesized by referring to four literatures as follows.

1) A synthetic method disclosed in Korean Patent No. 10-1488560 (Registered on Feb. 23, 2013) filed by Doosan Corporation was used. (See Reaction Scheme A)

2) The synthesis method disclosed in International Patent Application No. PCT-EP2015-068240 filed by BASF (Prior Application Date 2014 Aug. 8) was used. (See Reaction Scheme B)

3) The synthetic method disclosed in Chinese Patent Laid-Open Publication No. 2016-10316704 (filed on May 15, 2013) filed by Soochow University was used. (See Reaction Scheme C)

4) The synthesis method disclosed in Korean Patent Laid-Open Publication No. 2015-0130953 (filed by the priority date of 2014 Dec. 5) filed by LG Display Co., Ltd. was used. (See Synthesis of compound 6)

Synthesis Example of Sub 5 Synthesis Example of Sub 5-4

Sub 3 (72) (28 g, 45.55 mmol) was dissolved in toluene (228 ml) in a round bottom flask, and 2,3-dichlorobenzo[f]quinoxaline (12.48 g, 50.10 mmol), Pd₂(dba)₃ (1.25 g, 1.37 mmol), P(t-Bu)₃ (0.74 g, 3.64 mmol), NaOt-Bu (13.13 g, 136.64 mmol) were added and stirred at 100° C. After the reaction was completed, the reaction mixture was extracted with CH₂Cl₂ and water. The organic layer was dried over MgSO₄ and concentrated. The resulting compound was separated by silicagel column chromatography and recrystallized to obtain 15.07 g of the product. (yield: 40%)

Synthesis Example of Sub 5-10

(1) Synthesis of Sub 3-I-1

Sub 3 (73) (28 g, 66.11 mmol) was dissolved in toluene (694 ml) in a round bottom flask, and 1,4-dibromobenzene (17.16 g, 72.72 mmol), Pd₂(dba)₃ (0.91 g, 0.99 mmol), P(t-Bu)₃ (0.67 g, 3.31 mmol), NaOt-Bu (9.53 g, 99.17 mmol) were added and stirred at 100° C. After the reaction was completed, the reaction mixture was extracted with CH₂Cl₂ and water. The organic layer was dried over MgSO₄ and concentrated. The resulting compound was separated by silicagel column chromatography and recrystallized to obtain 27.16 g of the product. (yield: 71%)

(2) Synthesis of Sub 3-II-1

Sub 3-I-1 (27.16 g, 46.95 mmol) was dissolved in DMF (235 ml) in a round bottom flask, and Bis(pinacolato)diboron (13.11 g, 51.64 mmol), Pd(dppf)Cl₂ (1.03 g, 1.41 mmol), KOAc (13.82 g, 140.84 mmol) were added and stirred at 120° C. When the reaction is complete, the DMF is removed by distillation and extracted with CH₂Cl₂ and water. The organic layer was dried over MgSO₄ and concentrated. The resulting compound was separated by silicagel column chromatography and recrystallized to obtain 22.03 g of the product. (yield: 75%)

(3) Synthesis of Sub 5-10

Sub 3-II-1 (22.03 g, 35.21 mmol) was dissolved in THF (155 ml) in a round bottom flask, and 2,3-dichlorobenzo[4,5]thieno[2,3-b]pyrazine (8.98 g, 35.21 mmol), Pd(PPh₃)₄ (0.61 g, 0.53 mmol), K₂CO₃ (7.30 g, 52.82 mmol) and water (77.47 ml) were added and stirred at 80° C. When the reaction is complete, the DMF is removed by distillation and extracted with CH₂Cl₂ and water. The organic layer was dried over MgSO₄ and concentrated. The resulting compound was separated by silicagel column chromatography and recrystallized to obtain 9.61 g of the product. (yield: 38%)

Synthesis Example of Sub 5-24

Sub 3 (74) (31.61 g, 60.37 mmol), 2,3-dichlorobenzofuro[2,3-b]pyrazine (15.88 g, 66.41 mmol), Pd₂(dba)₃ (1.66 g, 1.81 mmol), P(t-Bu)₃ (0.98 g, 4.83 mmol), NaOt-Bu (17.41 g, 181.11 mmol), toluene (302 ml) were added, the same procedure as described in the synthesis method of Sub 5-4 was carried out to obtain 18.41 g of the product. (yield: 42%).

Synthesis Example of Sub 5-41

(1) Synthesis of Sub 3-I-2

Sub 3 (68) (53 g, 141.91 mmol), 1,3-dibromodibenzo[b,d]thiophene (48.54 g, 141.91 mmol), Pd₂(dba)₃ (1.95 g, 2.13 mmol), P(t-Bu)₃ (1.44 g, 7.10 mmol), NaOt-Bu (20.46 g, 212.87 mmol), toluene (1490 ml) were added, the same procedure as described in the synthesis method of Sub 3-I-1 was carried out to obtain 32.42 g of the product. (yield: 36%).

(2) Synthesis of Sub 3-II-2

Sub 3-I-2 (32 g, 50.42 mmol), DMF (252 ml), Bis(pinacolato)diboron (14.09 g, 55.47 mmol), Pd(dppf)Cl₂ (1.11 g, 1.51 mmol), KOAc (14.85 g, 151.27 mmol) were added, the same procedure as described in the synthesis method of Sub 3-II-1 was carried out to obtain 25.09 g of the product. (yield: 73%).

(3) Synthesis of Sub 5-41

Sub 3-II-2 (25 g, 36.67 mmol), 2,3-dichlorobenzofuro[2,3-b]pyrazine (8.77 g, 36.67 mmol), Pd(PPh₃)₄ (0.64 g, 0.55 mmol), K₂CO₃ (7.60 g, 55.01 mmol), THF (161 ml) and water (80 ml) were added, the same procedure as described in the synthesis method of Sub 5-10 was carried out to obtain 11.40 g of the product. (yield: 41%).

Synthesis Example of Sub 5-18

Sub 3 (70) (10.5 g, 29.38 mmol), 2,3-dichloroquinoxaline (5.85 g, 29.38 mmol), Pd₂(dba)₃ (0.40 g, 0.44 mmol), P(t-Bu)₃ (0.30 g, 1.47 mmol), NaOt-Bu (4.23 g, 44.07 mmol), toluene (308 ml) were added, the same procedure as described in the synthesis method of Sub 5-4 was carried out to obtain 11 g of the product. (yield: 72%).

Synthesis Example of Sub 5-44

Sub 3 (75) (20 g, 37.06 mmol), 2,3-dichlorobenzo[f]quinoxaline (9.23 g, 37.06 mmol), Pd₂(dba)₃ (0.51 g, 0.56 mmol), P(t-Bu)₃ (0.37 g, 1.85 mmol), NaOt-Bu (5.34 g, 55.59 mmol), toluene (389 ml) were added, the same procedure as described in the synthesis method of Sub 5-4 was carried out to obtain 11.15 g of the product. (yield: 40%).

Synthesis Example of Sub 5-52

Sub 3 (67) (12 g, 32.13 mmol), 2,3-dichloroquinoxaline (6.40 g, 32.13 mmol), Pd₂(dba)₃ (0.44 g, 0.48 mmol), P(t-Bu)₃ (0.33 g, 1.61 mmol), NaOt-Bu (4.63 g, 48.20 mmol), toluene (337 ml) were added, the same procedure as described in the synthesis method of Sub 5-4 was carried out to obtain 11.71 g of the product. (yield: 68%).

Synthesis Example of Sub 5-64

(1) Synthesis of Sub 3-I-3

Sub 3 (67) (39 g, 104.43 mmol), 3-bromo-7-iododibenzo[b,d]furan (38.95 g, 104.43 mmol), Pd₂(dba)₃ (1.43 g, 1.57 mmol), P(t-Bu)₃ (1.06 g, 5.22 mmol), NaOt-Bu (15.05 g, 156.64 mmol), toluene (1096 ml) were added, the same procedure as described in the synthesis method of Sub 3-I-1 was carried out to obtain 38.76 g of the product. (yield: 60%).

(2) Synthesis of Sub 3-II-3

Sub 3-I-3 (38.5 g, 62.24 mmol), DMF (311 ml), Bis(pinacolato)diboron (17.39 g, 68.47 mmol), Pd(dppf)Cl₂ (1.37 g, 1.87 mmol), KOAc (18.33 g, 186.73 mmol) were added, the same procedure as described in the synthesis method of Sub 3-II-1 was carried out to obtain 31.49 g of the product. (yield: 76%).

(3) Synthesis of Sub 5-64

Sub 3-II-3 (31 g, 46.57 mmol), 2,3-dichlorobenzofuro[2,3-b]pyrazine (11.13 g, 46.57 mmol), Pd(PPh₃)₄ (0.81 g, 0.70 mmol), K₂CO₃ (9.66 g, 69.86 mmol), THF (205 ml) and water (102 ml) were added, the same procedure as described in the synthesis method of Sub 5-4 was carried out to obtain 11.06 g of the product. (yield: 32%).

Synthesis Example of Sub 5-70

Sub 3 (76) (11 g, 25.37 mmol), 2,3-dichlorodibenzo[f,h]quinoxaline (7.59 g, 25.37 mmol), Pd₂(dba)₃ (0.35 g, 0.38 mmol), P(t-Bu)₃ (0.26 g, 1.27 mmol), NaOt-Bu (3.66 g, 38.06 mmol), toluene (266 ml) were added, the same procedure as described in the synthesis method of Sub 5-4 was carried out to obtain 11.13 g of the product. (yield: 63%).

Example of Sub 5

TABLE 5 compound FD-MS compound FD-MS Sub 5-1 m/z = 541.05 (C₃₂H₁₆ClN₃S₂ = 542.07) Sub 5-4 m/z = 782.14 (C₅₀H₂₇ClN₄S₂ = 783.36) Sub 5-10 m/z = 717.11 (C₄₆H₂₄ClN₃S₂ = 718.29) Sub 5-18 m/z = 519.11 (C₃₄H₁₈ClN₃O = 519.99) Sub 5-24 m/z = 725.15 (C₄₈H₂₄ClN₃O₃ = 726.19) Sub 5-41 m/z = 757.10 (C₄₈H₂₄ClN₃OS₂ = 758.31) Sub 5-44 m/z = 751.15 (C₅₀H₂₆ClN₃OS = 752.29) Sub 5-52 m/z = 535.09 (C₃₄H₁₈ClN₃S = 536.05) Sub 5-64 m/z = 741.13 (C₄₈H₂₄ClN₃O₂S = 742.25) Sub 5-70 m/z = 695.18 (C₄₈H₂₆ClN₃O = 696.21)

Synthesis of Sub 6

Sub 6 of Reaction Scheme 5 may be synthesized by a reaction route of the reaction scheme, but is not limited thereto.

Examples of the synthesis of specific compounds belonging to Sub 2 are as follows.

1. Synthesis Example of Sub 6-1

Starting material bromobenzene (29.16 g, 185.72 mmol) was dissolved in DMF (930 ml) in a round bottom flask, and Bis(pinacolato)diboron (51.88 g, 204.29 mmol), Pd(dppf)Cl₂ (4.55 g, 5.57 mmol), KOAc (54.68 g, 557.16 mmol) were added and stirred at 90° C. When the reaction is complete, the DMF is removed by distillation and extracted with CH₂Cl₂ and water. The organic layer was dried over MgSO₄ and concentrated. The resulting compound was separated by silicagel column chromatography and recrystallized to obtain 31.84 g of the product. (yield: 84%)

2. Synthesis Example of Sub 6-3

2-bromonaphthalene (21.53 g, 103.97 mmol), Bis(pinacolato)diboron (29.04 g, 114.37 mmol), Pd(dppf)Cl₂ (2.55 g, 3.12 mmol), KOAc (30.61 g, 311.92 mmol), DMF (520 ml) were added, the same procedure as described in the synthesis method of Sub 6-1 was carried out to obtain 21.14 g of the product. (yield: 80%).

3. Synthesis Example of Sub 6-5

3-bromo-1,1′-biphenyl (16.24 g, 69.67 mmol), Bis(pinacolato)diboron (19.46 g, 76.63 mmol), Pd(dppf)Cl₂ (1.71 g, 2.09 mmol), KOAc (20.51 g, 209.00 mmol), DMF (350 ml) were added, the same procedure as described in the synthesis method of Sub 6-1 was carried out to obtain 15.81 g of the product. (yield: 81%).

4. Synthesis Example of Sub 6-12

1-bromobenzene-2,3,4,5,6-d5 (10.85 g, 66.96 mmol), Bis(pinacolato)diboron (18.70 g, 73.65 mmol), Pd(dppf)Cl₂ (1.64 g, 2.01 mmol), KOAc (19.71 g, 200.88 mmol), DMF (335 ml) were added, the same procedure as described in the synthesis method of Sub 6-1 was carried out to obtain 10.22 g of the product. (yield: 73%).

5. Synthesis Example of Sub 6-21

4-bromodibenzo[b,d]thiophene (14.23 g, 54.08 mmol), Bis(pinacolato)diboron (15.11 g, 59.48 mmol), Pd(dppf)Cl₂ (1.32 g, 1.62 mmol), KOAc (15.92 g, 162.23 mmol), DMF (270 ml) were added, the same procedure as described in the synthesis method of Sub 6-1 was carried out to obtain 13.76 g of the product. (yield: 82%).

6. Synthesis Example of Sub 6-28

2-bromodibenzo[b,d]furan (16.35 g, 66.17 mmol), Bis(pinacolato)diboron (18.48 g, 72.79 mmol), Pd(dppf)Cl₂ (1.62 g, 1.99 mmol), KOAc (19.48 g, 198.51 mmol), DMF (330 ml) were added, the same procedure as described in the synthesis method of Sub 6-1 was carried out to obtain 16.74 g of the product. (yield: 86%).

7. Synthesis Example of Sub 6-32

3-bromo-9-phenyl-9H-carbazole (12.17 g, 37.77 mmol), Bis(pinacolato)diboron (10.55 g, 41.55 mmol), Pd(dppf)Cl₂ (0.93 g, 1.13 mmol), KOAc (11.12 g, 113.31 mmol), DMF (190 ml) were added, the same procedure as described in the synthesis method of Sub 6-1 was carried out to obtain 10.46 g of the product. (yield: 75%).

8. Synthesis Example of Sub 6-27

1-bromodibenzo[b,d]furan (16.78 g, 67.91 mmol), Bis(pinacolato)diboron (18.97 g, 74.70 mmol), Pd(dppf)Cl₂ (1.66 g, 2.04 mmol), KOAc (19.99 g, 203.73 mmol), DMF (340 ml) were added, the same procedure as described in the synthesis method of Sub 6-1 was carried out to obtain 15.98 g of the product. (yield: 80%).

9. Synthesis Example of Sub 6-36

1-bromothianthrene (13.31 g, 45.09 mmol), Bis(pinacolato)diboron (12.59 g, 49.60 mmol), Pd(dppf)Cl₂ (1.10 g, 1.35 mmol), KOAc (13.27 g, 135.26 mmol), DMF (225 ml) were added, the same procedure as described in the synthesis method of Sub 6-1 was carried out to obtain 10.34 g of the product. (yield: 67%).

The compounds belonging to Sub 6 may be, but not limited to, the following compounds, and Table 6 shows FD-MS (Field Desorption-Mass Spectrometry) values of some compounds belonging to Sub 6.

TABLE 6 compound FD-MS compound FD-MS Sub 6-1 m/z = 204.13 (C₁₂H₁₇BO₂ = 204.08) Sub 6-3 m/z = 254.15 (C₁₆H₁₉BO₂ = 254.14) Sub 6-5 m/z = 280.16 (C₁₈H₂₁BO₂ = 280.17) Sub 6-12 m/z = 209.16 (C₁₂H₁₂D₅BO₂ = 209.11) Sub 6-21 m/z = 310.12 (C₁₈H₁₉BO₂S = 310.22) Sub 6-28 m/z = 294.14 (C₁₈H₁₉BO₃ = 294.16) Sub 6-32 m/z = 369.19 (C₂₄H₂₄BNO₂ = 369.27) Sub 6-27 m/z = 294.14 (C₁₈H₁₉BO₃ = 294.16) Sub 6-36 m/z = 342.09 (C₁₈H₁₉BO₂S₂ = 342.28)

Synthesis Example of Final Products 2 Synthesis Example of 3-6

Sub 3 (1) (15.3 g, 47.3 mmol) was dissolved in toluene (500 mL) in a round bottom flask, and Sub 4-15 (14.8 g, 52.0 mmol), Pd₂(dba)₃ (2.4 g, 2.6 mmol), P(t-Bu)₃ (1.1 g, 5.2 mmol), NaOt-Bu (15 g, 156.1 mmol) were added and stirred at 100° C. When the reaction is complete, the DMF is removed by distillation and extracted with CH₂Cl₂ and water. The organic layer was dried over MgSO₄ and concentrated. The resulting compound was separated by silicagel column chromatography and recrystallized to obtain 17.0 g of the product. (yield: 68%)

Synthesis Example of 3-1

Sub 3 (7) (18.1 g, 47.3 mmol), toluene (500 mL), Sub 4-1 (8.2 g, 52.0 mmol), Pd₂(dba)₃ (2.0 g, 2.2 mmol), P(t-Bu)₃ (0.9 g, 4.4 mmol), NaOt-Bu (12.7 g, 132 mmol) were added, the same procedure as described in the synthesis method of 3-6 was carried out to obtain 15.6 g of the product. (yield: 72%).

Synthesis Example of 3-7

Sub 3 (1) (15.3 g, 47.3 mmol), toluene (500 mL), Sub 4-25 (15.4 g, 52.0 mmol), Pd₂(dba)₃ (2.4 g, 2.6 mmol), P(t-Bu)₃ (1.05 g, 5.2 mmol), NaOt-Bu (15 g, 156 mmol) were added, the same procedure as described in the synthesis method of 3-6 was carried out to obtain 19.3 g of the product. (yield: 70%).

Synthesis Example of 3-8

Sub 3 (1) (15.3 g, 47.3 mmol), toluene (500 mL), Sub 4-53 (15.1 g, 52 mmol), Pd₂(dba)₃ (2.4 g, 2.6 mmol), P(t-Bu)₃ (1.05 g, 5.2 mmol), NaOt-Bu (15 g, 156 mmol) were added, the same procedure as described in the synthesis method of 3-6 was carried out to obtain 19.4 g of the product. (yield: 71%).

Synthesis Example of 3-11

Sub 3 (13) (16.9 g, 47.3 mmol), toluene (500 mL), Sub 4-55 (16.1 g, 52.0 mmol), Pd₂(dba)₃ (2.4 g, 2.6 mmol), P(t-Bu)₃ (1.05 g, 5.2 mmol), NaOt-Bu (15 g, 156 mmol) were added, the same procedure as described in the synthesis method of 3-6 was carried out to obtain 20.2 g of the product. (yield: 73%).

Synthesis Example of 3-16

Sub 3 (17) (18.1 g, 47.2 mmol), toluene (500 mL), Sub 4-56 (16.7 g, 52.0 mmol), Pd₂(dba)₃ (2.4 g, 2.6 mmol), P(t-Bu)₃ (1.05 g, 5.2 mmol), NaOt-Bu (15 g, 156 mmol) were added, the same procedure as described in the synthesis method of 3-6 was carried out to obtain 19.8 g of the product. (yield: 67%).

Synthesis Example of 3-17

Sub 3 (59) (20.5 g, 47.4 mmol), toluene (500 mL), Sub 4-57 (13.7 g, 52.0 mmol), Pd₂(dba)₃ (2.4 g, 2.6 mmol), P(t-Bu)₃ (1.05 g, 5.2 mmol), NaOt-Bu (15 g, 156 mmol) were added, the same procedure as described in the synthesis method of 3-6 was carried out to obtain 20.1 g of the product. (yield: 69%).

Synthesis Example of 3-47

Sub 3 (45) (16.9 g, 47.3 mmol), toluene (500 mL), Sub 4-58 (14.6 g, 52.0 mmol), Pd₂(dba)₃ (2.4 g, 2.6 mmol), P(t-Bu)₃ (1.05 g, 5.2 mmol), NaOt-Bu (15 g, 156 mmol) were added, the same procedure as described in the synthesis method of 3-6 was carried out to obtain 20.5 g of the product. (yield: 72%).

Synthesis Example of 3-52

Sub 3 (50) (15.8 g, 47.4 mmol), toluene (500 mL), Sub 4-12 (20.2 g, 52.0 mmol), Pd₂(dba)₃ (2.4 g, 2.6 mmol), P(t-Bu)₃ (1.05 g, 5.2 mmol), NaOt-Bu (15 g, 156 mmol) were added, the same procedure as described in the synthesis method of 3-6 was carried out to obtain 20.0 g of the product. (yield: 66%).

Synthesis Example of 3-70

Sub 3 (60) (17.7 g, 47.4 mmol), toluene (500 mL), Sub 4-59 (17.8 g, 52.0 mmol), Pd₂(dba)₃ (2.4 g, 2.6 mmol), P(t-Bu)₃ (1.05 g, 5.2 mmol), NaOt-Bu (15 g, 156 mmol) were added, the same procedure as described in the synthesis method of 3-6 was carried out to obtain 22.8 g of the product. (yield: 71%).

Synthesis Example of 3-80

Sub 3 (61) (26.8 g, 47.4 mmol), toluene (500 mL), Sub 4-53 (15.1 g, 52.0 mmol), Pd₂(dba)₃ (2.4 g, 2.6 mmol), P(t-Bu)₃ (1.05 g, 5.2 mmol), NaOt-Bu (15 g, 156 mmol) were added, the same procedure as described in the synthesis method of 3-6 was carried out to obtain 26.4 g of the product. (yield: 68%).

Synthesis Example of 3-101

Sub 3 (67) (10 g, 26.78 mmol), toluene (281 ml), Sub 4-55 (7.09 g, 29.45 mmol), Pd₂(dba)₃ (0.74 g, 0.80 mmol), P(t-Bu)₃ (0.54 g, 2.68 mmol), NaOt-Bu (7.72 g, 80.33 mmol) were added, the same procedure as described in the synthesis method of 3-6 was carried out to obtain 11.91 g of the product. (yield: 77%).

TABLE 7 compound FD-MS compound FD-MS 3-1 m/z = 458.18 (C₃₄H₂₂N₂ = 458.56) 3-2 m/z = 449.12 (C₃₂H₁₉NS = 449.57) 3-3 m/z = 433.15 (C₃₂H₁₉NO = 433.51) 3-4 m/z = 535.23 (C₄₁H₂₉N = 535.69) 3-5 m/z = 399.11 (C₂₈H₁₇NS = 399.51) 3-6 m/z = 527.15 (C₃₆H₂₁N₃S = 527.65) 3-7 m/z = 583.12 (C₃₈H₂₁N₃S₂ = 583.73) 3-8 m/z = 577.16 (C₄₀H₂₃N₃S = 577.71) 3-9 m/z = 627.18 (C₄₄H₂₅N₃S = 627.77) 3-10 m/z = 475.14 (C₃₄H₂₁NS = 475.61) 3-11 m/z = 585.21 (C₄₄H₂₇NO = 585.71) 3-12 m/z = 509.21 (C₃₉H₂₇N = 509.65) 3-13 m/z = 509.19 (C₃₇H₂₃N₃ = 509.61) 3-14 m/z = 451..11 (C₃₀H₁₇N₃S = 451.55) 3-15 m/z = 588.20 (C₄₁H₂₄N₄O = 588.67) 3-16 m/z = 624.26 (C₄₇H₃₂N₂ = 624.79) 3-17 m/z = 614.18 (C₄₄H₂₆N₂S = 614.77) 3-18 m/z = 449.12 (C₃₂H₁₉NS = 449.57) 3-19 m/z = 573.17 (C₄₂H₂₃NO₂ = 573.65) 3-20 m/z = 664.26 (C₄₈H₃₂N₄ = 664.81) 3-21 m/z = 624.26 (C₄₇H₃₂N₂ = 624.79) 3-22 m/z = 603.18 (C₄₂H₂₅N₃S = 603.74) 3-23 m/z = 664.23 (C₄₇H₂₈N₄O = 664.77) 3-24 m/z = 737.28 (C₅₅H₃₅N₃ = 737.91) 3-25 m/z = 738.28 (C₅₄H₃₄N₄ = 738.89) 3-26 m/z = 679.21 (C₄₈H₂₉N₃S = 679.84) 3-27 m/z = 625.22 (C₄₅H₂₇N₃O = 625.73) 3-28 m/z = 575.24 (C₄₂H₂₉N₃ = 575.72) 3-29 m/z = 508.19 (C₃₈H₂₄N₂ = 508.62) 3-30 m/z = 449.12 (C₃₂H₁₉NS = 449.57) 3-31 m/z = 433.15 (C₃₂H₁₉NO = 433.51) 3-32 m/z = 531.20 (C₄₁H₂₅N = 531.66) 3-33 m/z = 608.23 (C₄₆H₂₈N₂ = 608.74) 3-34 m/z = 475.14 (C₃₄H₂₁NS = 475.61) 3-35 m/z = 384.13 (C₂₇H₁₆N₂O = 384.44) 3-36 m/z = 614.25 (C₄₄H₃₀N₄ = 614.75) 3-37 m/z = 508.19 (C₃₈H₂₄N₂ = 508.62) 3-38 m/z = 449.12 (C₃₂H₁₉NS = 449.57) 3-39 m/z = 433.15 (C₃₂H₁₉NO = 433.51) 3-40 m/z = 459.20 (C₃₅H₂₅N = 459.59) 3-41 m/z = 663.24 (C₄₇H₂₉N₅ = 663.78) 3-42 m/z = 603.18 (C₄₂H₂₅N₃S = 603.74) 3-43 m/z = 587.20 (C₄₂H₂₅N₃O = 587.68) 3-44 m/z = 613.25 (C₄₅H₃₁N₃ = 613.76) 3-45 m/z = 662.25 (C₄₈H₃₀N₄ = 662.80) 3-46 m/z = 577.16 (C₄₀H₂₃N₃S = 577.71) 3-47 m/z = 601.18 (C₄₂H₂₃N₃O₂ = 601.67) 3-48 m/z = 759.27 (C₅₇H₃₃N₃ = 759.91) 3-49 m/z = 589.22 (C₄₂H₂₆N₄ = 586.70) 3-50 m/z = 630.19 (C₄₃H₂₆N₄S = 630.77) 3-51 m/z = 613.22 (C₄₄H₂₇N₃O = 613.72) 3-52 m/z = 639.27 (C₄₇H₃₃N₃ = 639.80) 3-53 m/z = 508.19 (C₃₈H₂₄N₂ = 508.62) 3-54 m/z = 449.12 (C₃₂H₁₉NS = 449.57) 3-55 m/z = 433.15 (C₃₂H₁₉NO = 433.51) 3-56 m/z = 609.25 (C₄₇H₃₁N = 609.77) 3-57 m/z = 663.24 (C₄₇H₂₉N₅ = 663.78) 3-58 m/z = 604.17 (C₄₁H₂₄N₄S = 604.73) 3-59 m/z = 587.20 (C₄₂H₂₅N₃O = 587.68) 3-60 m/z613.25 (C₄₅H₃₁N₃ = 613.76) 3-61 m/z = 527.15 (C₃₆H₂₁N₃S = 527.65) 3-62 m/z = 603.18 (C₄₂H₂₅N₃S = 603.74) 3-63 m/z = 511.17 (C₃₆H₂₁N₃O = 511.58) 3-64 m/z = 587.24 (C₄₃H₂₉N₃ = 587.73) 3-65 m/z = 692.20 (C₄₈H₂₈N₄S = 692.84) 3-66 m/z = 577.16 (C₄₀H₂₃N₃S = 577.71) 3-67 m/z = 561.18 (C₄₀H₂₃N₃O = 561.64) 3-68 m/z = 653.19 (C₄₆H₂₇N₃S = 653.80) 3-69 m/z = 736.26 (C₅₄H₃₂N₄ = 736.88) 3-70 m/z = 677.19 (C₄₈H₂₇N₃S = 677.83) 3-71 m/z = 687.23 (C₅₀H₂₉N₃O = 687.80) 3-72 m/z = 743.24 (C₅₃H₃₃N₃S = 743.93) 3-73 m/z = 703.21 (C₅₀H₂₉N₃S = 703.86) 3-74 m/z = 603.18 (C₄₂H₂₅N₃S = 603.74) 3-75 m/z = 735.18 (C₅₀H₂₉N₃S₂ = 735.92) 3-76 m/z = 759.18 (C₅₂H₂₉N₃S₂ = 759.95) 3-77 m/z = 475.14 (C₃₄H₂₁NS = 475.61) 3-78 m/z = 616.20 (C₄₄H₂₈N₂S = 616.78) 3-79 m/z = 710.16 (C₄₇H₂₆N₄S₂ = 710.87) 3-80 m/z = 818.25 (C₅₈H₃₄N₄S = 819.00) 3-81 m/z = 603.18 (C₄₂H₂₅N₃S = 603.74) 3-82 m/z = 809.20 (C₅₆H₃₁N₃S₂ = 810.01) 3-83 m/z = 659.15 (C₄₄H₂₅N₃S₂ = 659.83) 3-84 m/z = 583.21 (C₄₀H₂₉N₃S = 583.75) 3-85 m/z = 844.27 (C₆₀H₃₆N₄S = 845.04) 3-86 m/z = 667.17 (C₄₆H₂₅N₃OS = 667.79) 3-87 m/z = 703.23 (C₅₀H₂₉N₃O₂ = 703.80) 3-88 m/z = 629.21 (C₄₄H₂₇N₃O₂ = 629.72) 3-89 m/z = 473.18 (C₃₅H₂₃NO = 473.58) 3-90 m/z = 600.22 (C₄₄H₂₈N₂O = 600.72) 3-91 m/z = 858.25 (C₆₀H₃₄N₄OS = 859.02) 3-92 m/z = 792.26 (C₅₅H₃₂N₆O = 792.90) 3-93 m/z = 514.24 (C₃₈H₃₀N₂ = 514.67) 3-94 m/z = 701.28 (C₅₂H₃₅N₃ = 701.87) 3-95 m/z = 700.26 (C₅₁H₃₂N₄ = 700.85) 3-96 m/z = 764.29 (C₅₆H₃₆N₄ = 764.93) 3-97 m/z = 700.29 (C₅₃H₃₆N₂ = 700.89 3-98 m/z = 576.26 (C₄₃H₃₂N₂ = 576.74) 3-99 m/z = 701.28 (C₅₂H₃₅N₃ = 701.87) 3-100 m/z = 761.28 (C₅₇H₃₅N₃ = 761.93)

Synthesis of Final Product 2′

Sub 4 (1 eq.) was dissolved in THF in a round bottom flask, and Sub 5 (1 eq.), Pd(PPh₃)₄ (0.04 eq.), NaOH (3 eq.) and water were added and stirred at 70° C. When the reaction is complete, the DMF is removed by distillation and extracted with CH₂Cl₂ and water. The organic layer was dried over MgSO₄ and concentrated. The resulting compound was separated by silicagel column chromatography and recrystallized to obtain Final product 2′.

Synthesis Example of P1-1 (when 3-101 was Prepared by Different Synthetic Methods)

Sub 5-1 (9 g, 16.79 mmol) was dissolved in THF (74 ml) in a round bottom flask, and Sub 6-1 (3.43 g, 16.79 mmol), Pd(PPh₃)₄ (0.78 g, 0.67 mmol), NaOH (2.01 g, 50.37 mmol) and water (37 ml) were added and stirred at 70° C. When the reaction is complete, the DMF is removed by distillation and extracted with CH₂Cl₂ and water. The organic layer was dried over MgSO₄ and concentrated. The resulting compound was separated by silicagel column chromatography and recrystallized to obtain 7.47 g of the product. (yield: 77%)

Synthesis Example of P1-14

Sub 5-4 (9 g, 10.88 mmol), THF (48 ml), Sub 6-1 (2.22 g, 10.88 mmol), Pd(PPh₃)₄ (0.5 g, 0.44 mmol), NaOH (1.31 g, 32.63 mmol) and water (24 ml) were added, the same procedure as described in the synthesis method of P1-1 was carried out to obtain 6.71 g of the product. (yield: 71%).

Synthesis Example of P1-30

Sub 5-10 (11 g, 15.31 mmol), THF (67 ml), Sub 6-18 (3.4 g, 15.31 mmol), Pd(PPh₃)₄ (0.71 g, 0.61 mmol), NaOH (1.84 g, 45.94 mmol) and water (34 ml) were added, the same procedure as described in the synthesis method of P1-1 was carried out to obtain 7.51 g of the product. (yield: 63%).

Synthesis Example of P1-45

Sub 5-1 (11 g, 20.52 mmol), THF (90 ml), Sub 6-34 (8.65 g, 20.52 mmol), Pd(PPh₃)₄ (0.95 g, 0.82 mmol), NaOH (2.46 g, 61.56 mmol) and water (45 ml) were added, the same procedure as described in the synthesis method of P1-1 was carried out to obtain 9.95 g of the product. (yield: 61%).

Synthesis Example of P2-7

Sub 5-24 (11 g, 15.15 mmol), THF (66 ml), Sub 6-20 (3.47 g, 15.15 mmol), Pd(PPh₃)₄ (0.7 g, 0.61 mmol), NaOH (1.82 g, 45.44 mmol) and water (33 ml) were added, the same procedure as described in the synthesis method of P1-1 was carried out to obtain 7.69 g of the product. (yield: 64%).

Synthesis Example of P3-16

Sub 5-29 (11 g, 18.77 mmol), THF (82 ml), Sub 6-29 (5.54 g, 18.77 mmol), Pd(PPh₃)₄ (0.87 g, 0.75 mmol), NaOH (2.25 g, 56.30 mmol) and water (41 ml) were added, the same procedure as described in the synthesis method of P1-1 was carried out to obtain 8.5 g of the product. (yield: 63%).

Synthesis Example of P4-3

Sub 5-44 (11 g, 14.62 mmol), THF (64 ml), Sub 6-22 (4.54 g, 14.62 mmol), Pd(PPh₃)₄ (0.68 g, 0.58 mmol), NaOH (1.75 g, 43.87 mmol) and water (32 ml) were added, the same procedure as described in the synthesis method of P1-1 was carried out to obtain 8.03 g of the product. (yield: 61%).

Synthesis Example of P5-9

Sub 5-52 (11 g, 20.52 mmol), THF (90 ml), Sub 6-32 (7.58 g, 20.52 mmol), Pd(PPh₃)₄ (0.95 g, 0.82 mmol), NaOH (2.46 g, 61.56 mmol) and water (45 ml) were added, the same procedure as described in the synthesis method of P1-1 was carried out to obtain 10.98 g of the product. (yield: 72%).

Synthesis Example of P5-25

Sub 5-57 (11 g, 14.32 mmol), THF (63 ml), Sub 6-1 (2.92 g, 14.32 mmol), Pd(PPh₃)₄ (0.66 g, 0.57 mmol), NaOH (1.72 g, 42.95 mmol) and water (31 ml) were added, the same procedure as described in the synthesis method of P1-1 was carried out to obtain 8.35 g of the product. (yield: 72%).

Synthesis Example of P5-41

Sub 5-64 (11 g, 14.82 mmol), THF (65 ml), Sub 6-1 (3.02 g, 14.82 mmol), Pd(PPh₃)₄ (0.69 g, 0.59 mmol), NaOH (1.78 g, 44.46 mmol) and water (32 ml) were added, the same procedure as described in the synthesis method of P1-1 was carried out to obtain 8.83 g of the product. (yield: 76%).

Synthesis Example of P6-15

Sub 5-78 (11 g, 21.15 mmol), THF (93 ml), Sub 6-1 (4.32 g, 21.15 mmol), Pd(PPh₃)₄ (0.98 g, 0.85 mmol), NaOH (2.54 g, 63.46 mmol) and water (46 ml) were added, the same procedure as described in the synthesis method of P1-1 was carried out to obtain 9.27 g of the product. (yield: 78%).

TABLE 8 compound FD-MS compound FD-MS P1-1 m/z = 577.16 (C₄₀H₂₃N₃S = 577.71) P1-2 m/z = 627.18 (C₄₄H₂₅N₃S = 627.77) P1-4 m/z = 868.27 (C₆₂H₃₆N₄S = 869.06) P1-6 m/z = 683.15 (C₂₆H₂₅N₃S₂ = 683.85) P1-8 m/z = 627.18 (C₄₄H₂₅N₃S = 627.77) P1-14 m/z = 868.27 (C₆₂H₃₆N₄S = 869.06) P1-16 m/z = 633.13 (C₄₂H₂₃N₃S₂ = 633.79) P1-26 m/z = 683.15 (C₂₆H₂₅N₃S₂ = 683.85) P1-30 m/z = 777.17 (C₅₂H₂₈FN₃S₂ = 777.94) P1-34 m/z = 667.17 (C₄₆H₂₅N₃OS = 667.79) P1-39 m/z = 693.19 (C₄₈H₂₇N₃OS = 693.82) P1-44 m/z = 578.16 (C₃₉H₂₂N₄S = 578.69) P1-45 m/z = 794.23 (C₅₄H₃₀N₆S = 794.94) P2-1 m/z = 561.18 (C₄₀H₂₃N₃O = 561.64) P2-4 m/z = 707.1 7 (C₄₈H₂₅N₃O₂S = 707.81) P2-5 m/z = 743.20 (C₅₂H₂₉N₃OS = 743.88) P2-7 m/z = 792.22 (C₅₅H₂₈N₄O₃ = 792.85) P2-9 m/z = 682.24 (C₄₈H₂₂D₅N₃O₂ = 682.79) P3-1 m/z = 577.16 (C₄₀H₂₃N₃S = 577.71) P3-2 m/z = 627.18 (C₄₄H₂₅N₃S = 627.77) P3-4 m/z = 653.19 (C₄₆H₂₇N₃S = 653.80) P3-15 m/z = 733.16 (C₅₀H₂₇N₃S₂ = 733.91) P3-16 m/z = 718.18 (C₄₉H₂₆N₄OS = 718.83) P3-19 m/z = 683.15 (C₂₆H₂₅N₃S₂ = 683.85) P3-36 m/z = 693.19 (C₄₈H₂₇N₃OS = 693.82) P3-44 m/z = 717.19 (C₅₀H₂₇N₃OS = 717.85) P3-45 m/z = 799.18 (C₅₄H₂₉N₃OS₂ = 799.97) P4-1 m/z = 561.18 (C₄₀H₂₃N₃O = 561.64) P4-2 m/z = 687.23 (C₅₀H₂₉N₃O = 687.80) P4-3 m/z = 899.21 (C₆₂H₃₃N₃OS₂ = 900.09) P4-9 m/z = 677.21 (C₄₈H₂₇N₃O₂ = 677.76) P5-1 m/z = 577.16 (C₄₀H₂₃N₃S = 577.71) P5-2 m/z = 627.18 (C₄₄H₂₅N₃S = 627.77) P5-7 m/z = 632.21 (C₄₄H₂₀D₅N₃S = 632.80) P5-8 m/z = 677.19 (C₄₈H₂₇N₃S = 677.83) P5-9 m/z = 742.22 (C₅₂H₃₀N₄S = 742.90) P5-11 m/z = 818.25 (C₅₈H₃₄N₄S = 819.00) P5-24 m/z = 723.14 (C₄₈H₂₅N₃OS₂ = 723.87) P5-25 m/z = 809.20 (C₅₆H₃₁N₃S₂ = 810.01) P5-26 m/z = 709.16 (C₄₈H₂₇N₃S₂ = 709.89) P5-31 m/z = 683.15 (C₂₆H₂₅N₃S₂ = 683.85) P5-41 m/z = 783.20 (C₅₄H₂₇₉N₃O₂S = 783.91) P5-42 m/z = 617.16 (C₄₂H₂₃N₃OS = 617.73) P5-44 m/z = 733.22 (C₅₁H₃₁N₃OS = 733.89) P6-1 m/z = 611.20 (C₄₄H₂₅N₃O = 611.70) P6-2 m/z = 651.19 (C₄₆H₂₅N₃O₂ = 651.73) P6-3 m/z = 743.20 (C₅₂H₂₉N₃OS = 743.88) P6-5 m/z = 713.25 (C₅₂H₃₁N₃O = 713.84) P6-7 m/z = 737.25 (C₅₄H₃₁N₃O = 737.86) P6-12 m/z = 918.30 (C₆₆H₃₈N₄O₂ = 919.06) P6-15 m/z = 561.18 (C₄₀H₂₃N₃O = 561.64)

Otherwise, the synthesis examples of the present invention represented by Formulas (1) and (2) have been described, but these are all based on the Buchwald-Hartwig cross coupling reaction, Suzuki cross-coupling reaction, Intramolecular acid-induced cyclization reaction (J. mater. Chem. 1999, 9, 2095), Pd(II)-catalyzed oxidative cyclization reaction (Org. Lett. 2011, 13, 5504), Grignard reaction, Cyclic Dehydration reaction and PPh3-mediated reductive cyclization reaction (J. Org. Chem. 2005, 70, 5014), and those skilled in the art will readily understand that the above reaction proceeds even when, besides the substituent specified in the specific synthesis example, other substituents (R¹ to R⁵, Ar¹ to Ar⁴, L¹ to L², X¹ to X²) defined in Formula (1) are bonded.

For example, Sub 1+Sub 2->Final Products 1 reaction in Reaction Scheme 1, the synthetic reaction of Sub 2 in Reaction Scheme 2, Sub 3+Sub 4->Final Products 2 reaction in Reaction Scheme 3 are all based on the Buchwald-Hartwig cross coupling reaction, and Sub 3-2+Sub 3-3->Sub 3-4 reaction in Reaction Scheme 4 is based on the Suzuki cross-coupling reaction, and Sub 3-4->Sub 3 in Reaction Scheme 4 is based on the PPh3-mediated reductive cyclization reaction (J. Org. Chem. 2005, 70, 5014.) The above reactions will proceed even if a substituent not specifically mentioned is bonded.

Evaluation of Manufacture of Organic Electric Element

Example 1) Manufacture and Evaluation of Red Organic Light Emitting Diode

First, on an ITO layer (anode) formed on a glass substrate, N¹-(naphthalen-2-yl)-N⁴,N⁴-bis(4-(naphthalen-2-yl(phenyl)amino)phenyl)-N¹-phenyl benzene-1,4-diamine (hereinafter will be abbreviated as 2-TNATA) was vacuum-deposited to form a hole injection layer with a thickness of 60 nm, and N,N′-bis(1-naphthalenyl)-N,N′-bis-phenyl-(1,1′-biphenyl)-4,4′-diamine (hereinafter will be abbreviated as NPB) was vacuum-deposited to form a hole transport layer with a thickness of 60 nm. On the hole transport layer, a mixture of the compounds represented by Formulas (1) and (2) as a host in a ratio of 3:7 was used as a host, and as a dopant, an emitting layer with a thickness of 30 nm was deposited on the hole transport layer by doping (piq)₂Ir(acac) [bis-(1-phenylisoquinolyl)iridium(III)acetylacetonate] with a weight of 95:5. (1,1′-bisphenyl)-4-olato)bis(2-methyl-8-quinolinolato)aluminum (hereinafter abbreviated as BAlq) was vacuum deposited as a hole blocking layer to a thickness of 10 nm, and tris(8-quinolinol)aluminum (hereinafter abbreviated as Alq3) was deposited to a thickness of 40 nm as an electron transport layer. After that, an alkali metal halide, LiF was vacuum deposited as an electron injection layer to a thickness of 0.2 nm, and Al was deposited to a thickness of 150 nm to form a cathode to manufacture an OLED.

To the OLEDs which were manufactured by examples and comparative examples, a forward bias direct current voltage was applied, and electroluminescent (EL) properties were measured using PR-650 of Photoresearch Co., and T95 life was measured using a life measuring apparatus manufactured by McScience Inc. with a reference luminance of 2500 cd/m². In the following table, the manufacture of a device and the results of evaluation are shown.

Comparative Examples 1 to 3

An organic electroluminescent device was manufactured in the same manner as in Example 1, except that the compound represented by Formula (2) was used as a host alone.

Comparative Example 4

An organic electroluminescent device was manufactured in the same manner as in Example 1, except that the comparative compound 1 was used as a host alone.

Comparative Example 5

An organic electroluminescent device was manufactured in the same manner as in Example 1, except that the comparative compound 2 was used as a host alone.

Comparative Example 6

An organic electroluminescent device was manufactured in the same manner as in Example 1, except that the comparative compound 3 was used as a host alone.

Comparative Example 7

An organic electroluminescent device was manufactured in the same manner as in Example 1, except that the comparative compound 4 was used as a host alone.

Comparative Example 8

An organic electroluminescent device was manufactured in the same manner as in Example 1, except that comparative compound 1 and 2 were mixed and used as a host.

Comparative Example 9

An organic electroluminescent device was manufactured in the same manner as in Example 1, except that comparative compound 3 and 4 were mixed and used as a host.

TABLE 9 Current Brightness Lifetime First host Second host Voltage Density (cd/m²) Efficiency T(95) comparative — compound (3-6) 6.1 15.7 2500.0 15.9 108.9 example (1) comparative — compound (3-61) 6.3 16.2 2500.0 15.5 104.2 example (2) comparative — compound (3-74) 6.4 16.2 2500.0 15.4 103.2 example (3) comparative — comparative 6.9 18.6 2500.0 13.4 84.3 example (4) compound 1- comparative — comparative 6.8 18.3 2500.0 13.7 83.3 example (5) compound 2 comparative — comparative 6.7 17.5 2500.0 14.3 87.4 example (6) compound 3 comparative — comparative 6.9 18.4 2500.0 13.6 82.9 example (7) compound 4 comparative comparative comparative 5.9 13.0 2500.0 19.3 103.8 example (8) compound 1 compound 2 comparative comparative comparative 5.6 10.5 2500.0 23.9 108.9 example (9) compound 3 compound 4 example (1) compound (1-4′) compound (3-6) 4.8 7.1 2500.0 35.0 136.1 example (2) compound (1-10′) compound (3-6) 4.7 7.1 2500.0 35.0 136.2 example (3) compound (1-16′) compound (3-6) 4.8 7.0 2500.0 35.7 136.2 example (4) compound (1-21′) compound (3-6) 4.6 6.6 2500.0 37.6 137.9 example (5) compound (1-33′) compound (3-6) 4.9 6.7 2500.0 37.4 137.1 example (6) compound (1-45′) compound (3-6) 4.5 6.6 2500.0 37.6 137.7 example (7) compound (1-48′) compound (3-6) 4.5 6.4 2500.0 39.3 138.2 example (8) compound (1-50′) compound (3-6) 4.8 5.9 2500.0 42.3 143.1 example (9) compound (1-55′) compound (3-6) 4.9 6.3 2500.0 39.9 139.8 example (10) compound (1-56′) compound (3-6) 4.6 6.4 2500.0 39.1 139.4 example (11) compound (1-4′) compound (3-7) 4.8 8.7 2500.0 28.6 125.1 example (12) compound (1-10′) compound (3-7) 4.7 8.7 2500.0 28.7 125.8 example (13) compound (1-16′) compound (3-7) 4.6 8.8 2500.0 28.3 125.9 example (14) compound (1-21′) compound (3-7) 4.6 8.5 2500.0 29.5 127.2 example (15) compound (1-33′) compound (3-7) 4.8 8.6 2500.0 29.0 127.5 example (16) compound (1-45′) compound (3-7) 4.8 8.5 2500.0 29.4 127.4 example (17) compound (1-48′) compound (3-7) 4.8 8.2 2500.0 30.6 128.4 example (18) compound (1-50′) compound (3-7) 4.6 8.3 2500.0 30.1 129.8 example (19) compound (1-55′) compound (3-7) 4.9 8.3 2500.0 30.2 128.1 example (20) compound (1-56′) compound (3-7) 5.0 8.2 2500.0 30.6 128.3 example (21) compound (1-4′) compound (3-8) 4.7 8.9 2500.0 28.2 126.3 example (22) compound (1-10′) compound (3-8) 4.9 8.9 2500.0 28.1 126.6 example (23) compound (1-16′) compound (3-8) 4.5 8.7 2500.0 28.6 125.8 example (24) compound (1-21′) compound (3-8) 4.7 8.6 2500.0 29.1 127.1 example (25) compound (1-33′) compound (3-8) 4.8 8.6 2500.0 29.1 127.2 example (26) compound (1-45′) compound (3-8) 4.6 8.4 2500.0 29.8 127.8 example (27) compound (1-48′) compound (3-8) 4.5 8.2 2500.0 30.6 128.8 example (28) compound (1-50′) compound (3-8) 4.7 8.3 2500.0 30.0 128.1 example (29) compound (1-55′) compound (3-8) 4.8 8.2 2500.0 30.6 128.5 example (30) compound (1-56′) compound (3-8) 4.9 8.2 2500.0 30.4 129.1 example (31) compound (1-4′) compound (3-9) 4.7 8.6 2500.0 29.0 125.3 example (32) compound (1-10′) compound (3-9) 4.8 8.9 2500.0 28.1 126.0 example (33) compound (1-16′) compound (3-9) 4.7 8.7 2500.0 28.7 125.8 example (34) compound (1-21′) compound (3-9) 4.7 8.4 2500.0 29.7 127.4 example (35) compound (1-33′) compound (3-9) 4.9 8.4 2500.0 29.9 127.9 example (36) compound (1-45′) compound (3-9) 4.9 8.5 2500.0 29.5 127.9 example (37) compound (1-48′) compound (3-9) 4.6 8.1 2500.0 30.7 129.1 example (38) compound (1-50′) compound (3-9) 4.9 8.3 2500.0 30.1 129.0 example (39) compound (1-55′) compound (3-9) 4.6 8.2 2500.0 30.5 128.7 example (40) compound (1-56′) compound (3-9) 4.7 8.1 2500.0 30.9 128.3 example (41) compound (1-4′) compound (3-15) 4.7 8.7 2500.0 28.7 126.9 example (42) compound (1-10′) compound (3-15) 4.9 8.8 2500.0 28.5 125.2 example (43) compound (1-16′) compound (3-15) 4.7 8.7 2500.0 28.6 125.1 example (44) compound (1-21′) compound (3-15) 5.0 8.4 2500.0 29.6 127.1 example (45) compound (1-33′) compound (3-15) 4.9 8.4 2500.0 29.8 127.2 example (46) compound (1-45′) compound (3-15) 4.9 8.4 2500.0 29.9 127.5 example (47) compound (1-48′) compound (3-15) 4.6 8.1 2500.0 30.7 128.2 example (48) compound (1-50′) compound (3-15) 4.5 8.3 2500.0 30.2 129.5 example (49) compound (1-55′) compound (3-15) 4.7 8.2 2500.0 30.4 128.9 example (50) compound (1-56′) compound (3-15) 4.9 8.2 2500.0 30.6 129.6 example (51) compound (1-4′) compound (3-37) 5.0 8.7 2500.0 28.8 127.0 example (52) compound (1-10′) compound (3-37) 4.8 8.8 2500.0 28.6 126.7 example (53) compound (1-16′) compound (3-37) 5.0 8.7 2500.0 28.8 125.5 example (54) compound (1-21′) compound (3-37) 4.8 8.5 2500.0 29.3 127.5 example (55) compound (1-33′) compound (3-37) 4.9 8.5 2500.0 29.3 127.2 example (56) compound (1-45′) compound (3-37) 4.8 8.5 2500.0 29.3 127.4 example (57) compound (1-48′) compound (3-37) 4.9 8.3 2500.0 30.3 129.1 example (58) compound (1-50′) compound (3-37) 4.7 8.1 2500.0 31.0 128.2 example (59) compound (1-55′) compound (3-37) 4.9 8.3 2500.0 30.3 129.2 example (60) compound (1-56′) compound (3-37) 4.6 8.1 2500.0 30.9 129.6 example (61) compound (1-4′) compound (3-46) 4.6 8.7 2500.0 28.8 126.1 example (62) compound (1-10′) compound (3-46) 4.8 8.7 2500.0 28.7 125.9 example (63) compound (1-16′) compound (3-46) 4.8 8.7 2500.0 28.9 126.2 example (64) compound (1-21′) compound (3-46) 4.9 8.6 2500.0 29.2 127.3 example (65) compound (1-33′) compound (3-46) 5.0 8.6 2500.0 29.0 127.1 example (66) compound (1-45′) compound (3-46) 4.7 8.4 2500.0 29.7 127.0 example (67) compound (1-48′) compound (3-46) 4.8 8.2 2500.0 30.3 129.9 example (68) compound (1-50′) compound (3-46) 4.5 8.3 2500.0 30.2 129.7 example (69) compound (1-55′) compound (3-46) 5.0 8.3 2500.0 30.1 128.3 example (70) compound (1-56′) compound (3-46) 5.0 8.1 2500.0 30.8 129.6 example (71) compound (1-4′) compound (3-50) 4.5 8.8 2500.0 28.5 126.1 example (72) compound (1-10′) compound (3-50) 4.7 8.9 2500.0 28.0 126.7 example (73) compound (1-16′) compound (3-50) 4.5 8.6 2500.0 28.9 125.1 example (74) compound (1-21′) compound (3-50) 4.6 8.4 2500.0 29.9 127.9 example (75) compound (1-33′) compound (3-50) 4.9 8.4 2500.0 29.8 127.4 example (76) compound (1-45′) compound (3-50) 4.7 8.6 2500.0 29.2 127.5 example (77) compound (1-48′) compound (3-50) 4.7 8.1 2500.0 30.8 128.3 example (78) compound (1-50′) compound (3-50) 4.6 8.3 2500.0 30.1 129.0 example (79) compound (1-55′) compound (3-50) 4.7 8.3 2500.0 30.2 128.0 example (80) compound (1-56′) compound (3-50) 4.7 8.2 2500.0 30.5 129.2 example (81) compound (1-4′) compound (3-61) 4.8 8.3 2500.0 30.2 130.5 example (82) compound (1-10′) compound (3-61) 4.6 8.2 2500.0 30.5 130.4 example (83) compound (1-16′) compound (3-61) 4.6 8.3 2500.0 30.2 130.6 example (84) compound (1-21′) compound (3-61) 4.8 7.8 2500.0 32.1 132.6 example (85) compound (1-33′) compound (3-61) 4.8 7.8 2500.0 32.2 132.2 example (86) compound (1-45′) compound (3-61) 5.0 7.7 2500.0 32.6 132.4 example (87) compound (1-48′) compound (3-61) 4.9 7.5 2500.0 33.3 134.7 example (88) compound (1-50′) compound (3-61) 4.7 7.5 2500.0 33.1 134.1 example (89) compound (1-55′) compound (3-61) 4.7 7.5 2500.0 33.1 133.8 example (90) compound (1-56′) compound (3-61) 4.8 7.2 2500.0 34.7 133.7 example (91) compound (1-4′) compound (3-74) 4.9 7.8 2500.0 32.1 126.8 example (92) compound (1-10′) compound (3-74) 4.8 8.9 2500.0 28.2 125.8 example(93) compound (1-16′) compound (3-74) 4.9 8.8 2500.0 28.4 126.3 example(94) compound (1-21′) compound (3-74) 4.5 8.5 2500.0 29.3 127.7 example(95) compound (1-33′) compound (3-74) 4.7 8.5 2500.0 29.3 127.2 example(96) compound (1-45′) compound (3-74) 4.8 8.5 2500.0 29.4 127.1 example(97) compound (1-48′) compound (3-74) 4.6 8.2 2500.0 30.6 128.9 example(98) compound (1-50′) compound (3-74) 4.7 8.1 2500.0 30.8 129.0 example(99) compound (1-55′) compound (3-74) 4.7 8.2 2500.0 30.7 128.7 example(100) compound (1-56′) compound (3-74) 4.9 8.1 2500.0 31.0 129.8

As can be seen from the results of Table 9, when the organic electric element material of the present invention represented by Formulas (1) and (2) is mixed and used as a phosphorescent host (Examples 1 to 100), it was confirmed that the driving voltage, efficiency, and life span were significantly improved as compared with the element (comparative examples 1 to 7) using a single material.

More specifically, in Comparative Examples 1 to 7, wherein the compounds of the present invention represented by Formula (2) and comparative compounds 1 to 4 are used alone as a phosphorescent host, Comparative Examples 1 to 3 using the compounds (3-6, 3-61, and 3-74) of the present invention had higher efficiency and longer life span than Comparative Examples 4 to 7 using the comparative compound.

Also, Comparative Example 8 and 9 wherein Comparative Compound 1 and 2 or Comparative Compound 3 and 4 were mixed and used as a phosphorescent host were found to exhibit higher efficiency than Comparative Examples 1 to 7 using the single substance. Comparing Comparative Example 8 with 9, Comparative Example 9 using a mixture containing a polycyclic compound having a different heteroatom (N, S) among the 5-membered compounds had higher efficiency than Comparative Example 8 mixed a 5-membered heterocyclic compound having the same nitrogen atom.

And it was confirmed that Example 1 to 100 using the mixture of the compound of Formula (1) and (2) as a host exhibited remarkably high efficiency and long life span than the Comparative Example 1 to 9.

On the basis of the above experimental results, the inventors of the present invention have found that, in the case of a mixture of the substance of Formulas (1) and (2), they have novel characteristics other than those for the respective materials, and have measured the PL lifetime using the substance of Formula (1), the substance of Formula (2), and the mixture of the present invention. As a result, it was confirmed that a new PL wavelength (556 nm) was formed when the compounds of Formulas (1) and (2) were mixed, and the decreasing and disappearing time of the newly formed PL wavelength increased from about 60 times to about 360 times compared to the reduction and disappearance times of substances Formula (1) and (2), respectively. It is considered when mixed with the compound of the present invention, not only electrons and holes are moved through the energy level of each substance, but also the efficiency and life span are increased by electron, hole transport or energy transfer by a new region (exciplex) having a new energy level formed due to mixing. As a result, when the mixture of the present invention is used, the mixed thin film is an important example showing exciplex energy transfer and light emitting process.

The reason why the combination of the present invention is superior to Comparative Examples 8 to 9 in which a comparative compound is used as a phosphorescent host is that the high Ti and high LUMO energy values improve the electron blocking ability and allow more holes to be moved to the emitting layer more quickly and easily when a compound represented by Formula (1) having a strong hole property is mixed with a polycyclic compound represented by Formula (2), which is characterized not only by electron but also by hole stability and high Ti. As a result, the charge balance in the emitting layer of holes and electrons is increased, so that light emission is well performed inside the emitting layer rather than at the interface of the hole transport layer, and therefore the deterioration in the HTL interface is also reduced, thereby maximizing the driving voltage, efficiency and life span of the device. Among the compounds represented by Formula (1), it has been confirmed that Dibenzofuran substituted compounds exhibits the best results in terms of the driving voltage, the efficiency and the lifetime, and Dibenzothiophen substituted compounds are also excellent in terms of efficiency due to their high refractive index. That is, it is concluded that the combination of Formula (1) and Formula (2) is electrochemically synergistic to improve the performance of the device as a whole.

Example 2) Manufacture and Evaluation of Red Organic Light Emitting Diode by Mixing Ratio

TABLE 10 Mixing ratio Second (first host:second Current Brightness Lifetime First host host host) Voltage Density (cd/m²) Efficiency T (95) example compound compound 2:8 4.7 7.9 2500.0 31.8 131.9 (101) (1-33′) (3-61) example compound compound 3:7 4.8 7.8 2500.0 32.2 132.2 (102) (1-33′) (3-61) example compound compound 4:6 5.0 8.4 2500.0 29.7 128.7 (103) (1-33′) (3-61) example compound compound 5:5 5.1 9.1 2500.0 27.4 124.1 (104) (1-33′) (3-61) example compound compound 2:8 4.8 5.8 2500.0 43.2 145.6 (105) (1-50′) (3-6) example compound compound 3:7 4.8 5.9 2500.0 42.3 143.1 (106) (1-50′) (3-6) example compound compound 4:6 5.1 6.5 2500.0 38.4 139.1 (107) (1-50′) (3-6) example compound compound 5:5 5.3 7.1 2500.0 35.0 137.9 (108) (1-50′) (3-6)

As shown in Table 10, the mixture of the compound of the present invention was measured by fabricating the device in (2:8, 3:7, 4:6, 5:5). To explain the results in detail, in the result of the mixture of the compound 1-54 and 3-6, the results of the driving voltage, the efficiency and the life span were similarly excellent at 2:8 and 3:7, but as the ratio of the first host increases, such as 4:6 and 5:5, the results of the driving voltage, the efficiency and the life span are gradually decreased, this was also the same in the result of the mixture of the compound 1-33′ and 3-61. This can be explained by the fact that the charge balance in the emitting layer is maximized when an appropriate amount of the compound represented by Formula (1) having strong hole properties such as 2:8 and 3:7 is mixed.

Although exemplary embodiments of the present invention have been described for illustrative purposes, those skilled in the art will appreciate that various modifications, additions and substitutions are possible, without departing from the scope and spirit of the invention as disclosed in the accompanying claims. Therefore, the embodiment disclosed in the present invention is intended to illustrate the scope of the technical idea of the present invention, and the scope of the present invention is not limited by the embodiment.

The scope of the present invention shall be construed on the basis of the accompanying claims, and it shall be construed that all of the technical ideas included within the scope equivalent to the claims belong to the present invention. 

What is claimed is:
 1. An organic electric element comprising a first electrode, a second electrode, and an organic material layer formed between the first electrode and the second electrode, wherein the organic material layer comprises an emitting layer, wherein the emitting layer is a phosphorescent light emitting layer and comprises a first host compound represented by Formula (1) and a second host compound represented by Formula (2):

wherein, 1) Ar¹, Ar², Ar³, and Ar⁴ are each independently selected from the group consisting of a C₆-C₆₀ aryl group; a fluorenyl group; a C₂-C₆₀ heterocyclic group including at least one hetero atom of O, N, S, Si or P; a fused ring group of a C₃-C₆₀ aliphatic ring and a C₆-C₆₀ aromatic ring; a C₁-C₅₀ alkyl group; a C₂-C₂₀ alkenyl group; a C₂-C₂₀ alkynyl group; a C₁-C₃₀ alkoxyl group; a C₆-C₃₀ aryloxy group; 2) c and e are integer of 0 to 10, and d is an integer of 0 to 2, and R³, R⁴ and R⁵ are the same or different from each other, and are each independently selected from the group consisting of deuterium; halogen; a C₆-C₆₀ aryl group; a fluorenyl group; a C₂-C₆₀ heterocyclic group including at least one heteroatom of O, N, S, Si or P; a fused ring group of a C₃-C₆₀ aliphatic ring and a C₆-C₆₀ aromatic ring; a C₁-C₅₀ alkyl group; a C₂-C₂₀ alkenyl group; a C₂-C₂₀ alkynyl group; a C₁-C₃₀ alkoxyl group; a C₆-C₃₀ aryloxy group; and -L′-N(R_(a))(R_(b)); (wherein, L′ is selected from the group consisting of a single bond; a C₆-C₆₀ arylene group; a fluorenylene group; a fused ring group of a C₃-C₆₀ aliphatic ring and a C₆-C₆₀ aromatic ring; and a C₂-C₆₀ heterocyclic, and R_(a) and R_(b) are independently selected from the group consisting of a C₆-C₆₀ aryl group; a fluorenyl group; a fused ring group of a C₃-C₆₀ aliphatic ring and a C₆-C₆₀ aromatic ring; and a C₂-C₆₀ heterocyclic group containing at least one hetero atom of O, N, S, Si, or P), or in case c, d and e are 2 or more, R³, R⁴ and R⁵ are each in plural being the same or different, and a plurality of R³ or a plurality of R⁴ or a plurality of R⁵ combine to each other to form a ring; 3) L¹, L², L³ and L⁴ are selected from the group consisting of a single bond, a C₆-C₆₀ arylene group, and a fluorenylene group; a fused ring group of a C₃-C₆₀ aliphatic ring and a C₆-C₆₀ aromatic ring; and a C₂-C₆₀ heterocyclic group; 4) A and B are each independently a C₆-C₆₀ aryl group or a C₂-C₂₀ heterocyclic group, wherein both A and B are a substituted or unsubstituted C₆ aryl group (phenyl group), d is 2, and R⁴s are bonded to each other to form a ring to form an aromatic or hetero ring; 5) i and j are 0 or 1, with the proviso that i+j is 1 or more, and when i or j is 0, it means a direct bond; 6) X¹ and X² are independently NR′, O, S, or CR′R″; wherein R′ and R″ are independently hydrogen; a C₆-C₆₀ aryl group; a fluorenyl group; a C₃-C₆₀ heterocyclic group; or a C₁-C₅₀ alkyl group; wherein R′ and R″ may combine to each other to form a spiro, (wherein, the aryl group, fluorenyl group, arylene group, heterocyclic group, fused ring group, alkyl group, alkenyl group, alkoxy group and aryloxy group may be substituted with one or more substituents selected from the group consisting of deuterium; halogen; a silane group substituted or unsubstituted with C₁-C₂₀ alkyl group or C₆-C₂₀ aryl group; siloxane group; boron group; germanium group; cyano group; nitro group; -L′-N(R_(a))(R_(b)); a C₁-C₂₀ alkylthio group; C₁-C₂₀ alkoxyl group; C₁-C₂₀ alkyl group; C₂-C₂₀ alkenyl group; C₂-C₂₀ alkynyl group; C₆-C₂₀ aryl group; C₆-C₂₀ aryl group substituted with deuterium; a fluorenyl group; C₂-C₂₀ heterocyclic group; C₃-C₂₀ cycloalkyl group; C₇-C₂₀ arylalkyl group and C₈-C₂₀ arylalkenyl group, wherein the substituents may combine each other and form a saturated or unsaturated ring, wherein the term ‘ring’ means C₃-C₆₀ aliphatic ring or C₆-C₆₀ aromatic ring or a C₂-C₆₀ heterocyclic ring or a fused ring formed by the combination of thereof.
 2. An organic electric element comprising: the first host compound represented by Formula (1) is represented by any one of the following Formulas (3) to (5):

wherein, 1) L¹, L³, L⁴, L′, R^(a), R^(b), Ar² and Ar³ are the same as defined in claim 1, 2) X³ is O or S, 3) a is an of 0 to 4, and b is an integer of 0 to 3, and R¹ and R² are the same or different from each other, and are each independently selected from the group consisting of deuterium; halogen; a C₆-C₆₀ aryl group; a fluorenyl group; a C₂-C₆₀ heterocyclic group including at least one heteroatom of O, N, S, Si or P; a fused ring group of a C₃-C₆₀ aliphatic ring and a C₆-C₆₀ aromatic ring; a C₁-C₅₀ alkyl group; a C₂-C₂₀ alkenyl group; a C₂-C₂₀ alkynyl group; a C₁-C₃₀ alkoxyl group; a C₆-C₃₀ aryloxy group; and -L′-N(R_(a))(R_(b)); or in case a and b are 2 or more, and R¹ and R² are each in plural being the same or different, and a plurality of R¹ or a plurality of R² combine to each other to form a ring.
 3. The organic electric element according to claim 1, wherein the compound represented by Formula (1) is represented by any one of the following Formulas (6) to (14):

wherein, L¹, L³, L⁴, Ar², Ar³, R¹, R², a and b are the same as defined in claim
 1. 4. The organic electric element according to claim 1, wherein the first host compound represented by Formula (1) is represented by any one of the following Formulas (15) to (23):

wherein, L¹, L³, L⁴, Ar², Ar³, R¹, R², a and b are the same as defined in claim
 1. 5. The organic electric element according to claim 1, wherein Ar¹, Ar² and Ar³ are all C₆-C₂₄ aryl groups and L¹, L³ and L⁴ are single bonds or all C₆-C₂₄ aryl groups.
 6. The organic electric element according to claim 1, wherein the first host compound represented by Formula (1) is represented by any one of the following Formulas (24) to (26):

wherein 1) L¹, L³, L⁴, L′, R^(a), R^(b), Ar² and Ar³ are the same as defined in claim 1, 2) Ar⁵ and Ar⁶ are each independently selected from the group consisting of a C₆-C₆₀ aryl group; a C₂-C₆₀ heterocyclic group including at least one heteroatom of O, N, S, Si or P; a fused ring group of a C₃-C₆₀ aliphatic ring and a C₆-C₆₀ aromatic ring; a C₁-C₅₀ alkyl group; a C₂-C₂₀ alkenyl group; a C₂-C₂₀ alkynyl group; a C₁-C₃₀ alkoxyl group; a C₆-C₃₀ aryloxy group; and L′-N(R_(a))(R_(b)).
 7. The organic electric element according to claim 1, wherein L¹, L³ and L⁴ in Formula (1) of the present invention are selected from the group consisting of the following Formulas (A-1) to (A-12):

wherein, 1) a′, c′, d′ and e′ are an integer of 0 to 4, and b′ is an integer of 0 to 6, and f′ and g′ are integer of 0 to 3, and h′ is an integer of 0 to 1, 2) R⁶, R⁷ and R⁸ are the same or different from each other, and are each independently selected from the group consisting of deuterium; halogen; a C₆-C₆₀ aryl group; a fluorenyl group; a C₂-C₆₀ heterocyclic group including at least one heteroatom of O, N, S, Si or P; a fused ring group of a C₃-C₆₀ aliphatic ring and a C₆-C₆₀ aromatic ring; a C₁-C₅₀ alkyl group; a C₂-C₂₀ alkenyl group; a C₂-C₂₀ alkynyl group; a C₁-C₃₀ alkoxyl group; a C₆-C₃₀ aryloxy group; and -L′-N(R_(a))(R_(b)); or wherein f′ and g′ are two or more, R⁶, R⁷ and R⁸ are the same as or different from each other, and a plurality of R⁶ or a plurality of R⁷ or adjacent R⁶ and R⁷ may combine to each other to form an aromatic or a heteroaromatic ring, 3) Y is NR′, O, S or CR′R″, L′, R^(a), R^(b), Ar² and Ar³ are the same as defined above, 4) Z¹, Z² and Z³ are CR′ or N and at least one is N.
 8. The organic electric element according to claim 1, wherein at least one of L¹, L³, and L⁴ in Formula (1) is a phenyl group and is substituted with an m (meta)-position.
 9. The organic electric element according to claim 1, wherein the second host compound represented by Formula (2) comprises a compound represented by the following Formula (27) or (28):

wherein, R³, R⁴, R⁵, Ar⁴, L², c, d, e, A, B, X¹ and X² are the same as defined in claim
 1. 10. The organic electric element according to claim 1, wherein A and B in Formula (2) are selected from the group consisting of the following Formulas (B-1) to (B-7):

wherein, 1) Z⁴ to Z⁵⁰ are CR′ or N, 2) R′ is the same as defined above, 3) * indicates the position to be condensed.
 11. The organic electric element according to claim 1, wherein d in Formula (2) is 2 and R⁴ is bonded to form a ring to form an aromatic group or a heterocyclic ring.
 12. The organic electric element according to claim 1, wherein the second host compound represented by Formula (2) includes a compound represented by any of the following Formulas (29) to (48):

wherein, Ar⁴, X¹, X², R³, R⁴, R⁵, L², c, d, and e are the same as defined in claim
 1. 13. The organic electric element according to claim 1, wherein the second host compound represented by Formula (2) comprises any of compounds represented by the following Formulas (49) to (56):

wherein, R³, R⁴, R⁵, R′, R″, L², Ar⁴, c, d, e, A and B are the same as defined in claim
 1. 14. The organic electric element according to claim 1, wherein the first host compound represented by Formula (1) is one of the following Compounds 1-1′ to 1-82′:


15. The organic electric element according to claim 1, wherein the first host compound represented by Formula (2) is one of the following compounds:


16. The organic electric element according to claim 1, wherein the emitting layer is a phosphorescent light emitting layer.
 17. The organic electric element according to claim 1, wherein the compounds represented by Formula (1) and (2) are mixed in a ratio of 1:9 to 9:1 to be included in the emitting layer.
 18. The organic electric element according to claim 1, wherein the compound represented by Formula (1) and (2) are mixed in a ratio of 1:9 to 5:5 to be included in the emitting layer.
 19. The organic electric element according to claim 1, wherein the compound represented by Formula (1) and (2) are mixed in a ratio of 2:8 or 3:7 to be included in the emitting layer.
 20. An electronic device comprising a display apparatus comprising the organic electric element according to claim 1; and a driving part configured to drive the display apparatus.
 21. The electronic device according to claim 20, wherein the organic electric element is at least one of an OLED, an organic solar cell, an organic photo conductor, an organic transistor and a device for monochromic or white illumination. 